研究者詳細 - 岡内　辰夫

論文 - 岡内　辰夫

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A Convenient Method for Synthesizing 1-Alkyl-2-Acyl-sn-Glycero-3-Phosphoethanolamines 査読有り国際誌

Okauchi T., Tsubaki K., Higuma Y., Shimooka H., Kitamura M.

Synthesis (Germany) 56 ( 11 ) 1787 - 1792 2024年02月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

A convenient method for synthesizing 1-Alkyl-2-Acyl-sn-glycero-3-phosphoethanolamines starting from an optical active alcohol is described. In this method, the phosphate group was introduced through the transesterification that we developed, and a protected 1-Alkyl-2-lyso-GPE was employed as an intermediate. This compound is stable and serves as a common intermidiate for the synthesis of various 1-Alkyl-2-Acyl-GPEs with different acyl groups.

DOI： 10.1055/a-2257-0684

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KIT-13, a novel plasmalogen derivative, attenuates neuroinflammation and amplifies cognition 査読有り

Hossain M.S., Mawatari S., Honsho M., Okauchi T., Fujino T.

Frontiers in Cell and Developmental Biology 12 2024年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

Plasmalogens (Pls) are specialized phospholipids integral to brain health, whose decline due to aging and stress contributes to cognitive impairment and neuroinflammation. This study explores the potential of a novel Pls derivative, KIT-13 (1-O-octadecyl-2-arachidonoyl-sn-glycerol-3-phosphoethanolamine), in mitigating neuroinflammation and enhancing cognition. When administered to mice, KIT-13 exhibited potent memory enhancement attributed to upregulated brain-derived neurotrophic factor (BDNF), a key player in cognitive processes. In vitro experiments with neuronal cells revealed KIT-13’s ability to induce robust cellular signaling, surpassing natural plasmalogens. KIT-13 also promoted neurogenesis and inhibited apoptosis of neuronal-like cells, highlighting its potential in fostering neuronal growth and plasticity. Additionally, KIT-13 treatments reduced pro-inflammatory cytokine expression and attenuated glial activation in the brain. KIT-13’s superior efficacy over natural Pls positions it as a promising therapeutic candidate for neurodegenerative conditions such as Alzheimer’s disease, characterized by cognitive decline and neuroinflammation. This study presents KIT-13 as an innovative approach for addressing cognitive impairment and neuroinflammatory pathologies.

DOI： 10.3389/fcell.2024.1443536

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Diazo-Transfer Reaction of Nonactivated Ketones with 2-Azido-1,3-bis(2,6-diisopropylphenyl)imidazolium Hexafluorophosphate (IPrAP) 査読有り国際誌

Kitamura M., Ohtsuka K., Eto T., Tsuzaki M., Wada M., Shimooka H., Okauchi T.

Journal of Organic Chemistry 88 ( 21 ) 15494 - 15500 2023年11月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

The diazo-transfer reaction of nonactivated ketone under mild reaction conditions was developed. Various nonactivated ketones such as aryl methyl ketones, sec-alkyl methyl ketones, and cyclic ketones were transformed into their corresponding α-diazoketones in one step by treating 2-azido-1,3-bis(2,6-diisopropylphenyl)imidazolium hexafluorophosphate (IPrAP) in the presence of iPr2NH in ethylene glycol. In the reaction of IPrAP with prim-alkyl methyl ketone and prim-alkyl aryl ketones, migratory amidation proceeded under the reaction conditions to afford the corresponding amides.

DOI： 10.1021/acs.joc.3c01743

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Synthesis of an Ortho-Functionalized Tetrafluorinated Azobenzene Phosphoramidite for Incorporation into a Tetrafluorinated Azobenzene-Containing siRNA for Photocontrolled Gene Silencing 査読有り国際誌

Hammill M.L.(Ontario Tech University), Tsubaki K., Kitamura M., Okauchi T., Desaulniers J.P.(Ontario Tech University)

Current Protocols 3 ( 10 ) e874 2023年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

This article presents the detailed synthesis and characterization protocols for an ortho-functionalized tetrafluorinated azobenzene containing siRNA, which has photoswitchable properties. To design this tetrafluorinated azobenzene scaffold, several synthetic steps are performed to generate a symmetrical tetrafluorinated azobenzene diol. This diol is treated with dimethoxytrityl chloride (DMT-Cl) to protect one of the alcohols. Next, the DMT-protected tetrafluorinated monoalcohol is phosphitylated to afford the DMT-phosphoramidite building block used for solid-phase synthesis. This paper also contains the detailed biophysical characterization, biological testing, and photo-switching protocols of an ortho-functionalized fluorinated azobenzene containing siRNA (F-siRNA), which has photoswitchable properties that can be controlled with visible light. First, the F-siRNA was characterized by annealing the sense and antisense strands together and then measuring the circular dichroism (CD) profile and melting temperature (Tm) of the duplexes. Second, biological testing of the F-siRNA is performed in cell culture to determine their gene silencing efficacy. Finally, their gene-silencing activities are measured after exposure to green light to inactivate the F-siRNA, followed by blue light, which reactivates the F-siRNA. The F-siRNA can be kept inactive for up to 72 hr and reactivated at any time within this 72-hr window. © 2023 Wiley Periodicals LLC.

DOI： 10.1002/cpz1.874

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Formal synthesis of isoquinocyclinone using ortho-alkoxycarbonylmethylation of anthranol via diazoquinone 査読有り国際誌

Mitsuru Kitamura, Noriyuki Fukuzumi, Masayuki Shinagawa, Keiichiro Araki, Yutaro Shimizu, Shuhei Takahashi, Takumi Iwata, Hirokazu Shimooka, Tatsuo Okauchi

Tetrahedron Letters ( Elsevier ) 125 154618 2023年06月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

In this study, a formal synthesis of isoquinocyclinone is reported. Synthesis of key intermediate lactone 6, an intermediate in Koert's s total synthesis of isoquinocyclinone, was succeeded. The lactone 6 was synthesized by using our developed diazo-transfer reaction of anthranol with 2-azido-1,3-dimethylimidazolinium chloride (ADMC) and alkoxycarbonylmethylation of diazoquinone as key reactions.

DOI： 10.1016/j.tetlet.2023.154618

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Conversion of η<sup>4</sup>-(Vinylketene)iron complexes to η<sup>4</sup>-(Vinylketenimine)iron complexes using titanium chloride and amines 査読有り国際誌

Okauchi T., Teratani K., Nakagawa T., Ichimura T., Shimooka H., Kitamura M.

Journal of Organometallic Chemistry 990 2023年05月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

We developed a one-pot convenient method for the synthesis of η4-(vinylketenimine)iron complexes using η4-(vinylketene)iron complexes. This method does not require toxic reagents or prior preparation of corresponding reagents. The (vinylketene)iron complex is readily converted to (vinylketene)iron complex by mixing TiCl4 and a commercially available amine.

DOI： 10.1016/j.jorganchem.2023.122672

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Synthesis of Dinucleotide Non-Symmetrical Triester Phosphate Phosphoramidites and Their Incorporation Within Oligonucleotides 査読有り国際誌

Desaulniers, J.-P.(Ontario Tech University); Tsubaki, K.; Hammill, M. L.(Ontario Tech University); Kitamura, M.; Okauchi, T.

Current Protocols ( Willy ) 3 ( 5 ) e784 2023年05月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

In this protocol article, the synthesis of dinucleotide non-symmetrical triester phosphate phosphoramidites will be highlighted. Specifically, we use a selective transesterification starting with tris(2,2,2-trifluoroethyl) phosphate to afford a dinucleotide derivative phosphate ester. Substitution of the final trifluoroethyl group with various alcohols affords a dinucleotide triester phosphate with a hydrophobic group, which can then be deprotected and converted to a phosphoramidite for incorporation within oligonucleotides.

DOI： 10.1002/cpz1.784

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Synthesis, Derivatization and Photochemical Control of an ortho-Functionalized Tetrafluorinated Azobenzene-Modified siRNA 査読有り国際誌

Hammill M.L.(Ontario Tech University), Tsubaki K., Wang Y.(Ontario Tech University), Islam G.(Ontario Tech University), Kitamura M., Okauchi T., Desaulniers J.P.(Ontario Tech University)

ChemBioChem 23 ( 20 ) e202200386 2022年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

We report the synthesis of an ortho-functionalized tetrafluorinated azobenzene phosphoramidite for its site-specific incorporation into RNA. The tetrafluorinated azobenzene is embedded within the antisense strand of an siRNA duplex to form an ortho-functionalized tetrafluorinated azobenzene-containing siRNA (F-siRNAzo). The F-siRNAzo is inactivated via trans to cis conversion with green light (530 nm), and reactivated with blue light (470 nm) via cis to trans conversion in cell culture. The long half-life and stability of the tetrafluorinated azobenzene unit allows for reversible control of the F-siRNAzo in cell culture for up 72 hours.

DOI： 10.1002/cbic.202200386

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Formal Synthesis of Teadenols via Pd-catalyzed 6- endo Cyclization of Epoxyphenol 査読有り国際誌

Kitamura M., Suetake H., Hoshino K., Higashijima Y., Kisanuki M., Yuasa R., Yamaguchi Y., Shimazu T., Koga N., Hamada H., Miyori N., Shimooka H., Okauchi T.

Synlett 33 ( 15 ) 1523 - 1526 2022年08月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

Formal synthesis of teadenol A and B was achieved via Pd-catalyzed 6- endo cyclization of phenol having vinylepoxide moiety as a key reaction. Although 5- exo and 6- endo cyclizations compete for the cyclization of epoxides with a nucleophilic moiety at the 5-position, 6- endo cyclization can be realized by using a palladium catalyst.

DOI： 10.1055/a-1890-8287

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Synthesis of Diazoquinones and Azidophenols via Diazo-Transfer Reaction of Phenols 査読有り国際誌

Mitsuru Kitamura, Takashi Eto, Kazushige Konai, Shuhei Takahashi, Hirokazu Shimooka, Tatsuo Okauchi

European Journal of Organic Chemistry 2022 ( 18 ) 2022年04月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

An efficient diazo-transfer reaction of phenol is described. o-Quinone diazide (diazoquione) were synthesized from phenol by the diazo-transfer reaction using 2-azido-1,3-bis(2,6-diisopropylphenyl)imidazolium hexafluorophosphate (IPrAP), which is safe and stable crystalline, in MeOH in the presence of iPr2NH or DMAP. In addition, diazoquinones reacted with sodium azide smoothly in 2-methoxyethanol to give azidophenols in high yields.

DOI： 10.1002/ejoc.202200307

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SiRNAs with Neutral Phosphate Triester Hydrocarbon Tails Exhibit Carrier-Free Gene-Silencing Activity 査読有り国際誌

Matthew L. Hammill(Ontario Tech University), Kouta Tsubaki, Lidya Salim(Ontario Tech University), Andrew J. Varley(Ontario Tech University), Ifrodet Giorgees(Ontario Tech University), Mitsuru Kitamura, Tatsuo Okauchi, Jean-Paul Desaulniers(Ontario Tech University)

ACS Medicinal Chemistry Letters ( American Chemical Society ) 13 ( 4 ) 695 - 700 2022年04月

記述言語：英語掲載種別：研究論文（学術雑誌）

Short interfering RNAs (siRNAs) show promise as gene-silencing therapeutics, but their cellular uptake remains a challenge. We have recently shown the synthesis of siRNAs bearing a single neutral phenylethyl phosphotriester linkage within the sense strand. Here, we report the synthesis of siRNAs bearing three different hydrophobic phosphate triester linkages at key positions within the sense strand and assess their gene silencing in the absence of a transfection carrier. The best siRNAs bearing hydrophobic phosphate triester tails were not aromatic and exhibited effective gene silencing (IC50 ≈ 56–141 nM), whereas the aromatic derivative with three hydrophobic tails did not exhibit carrier-free gene silencing.

DOI： 10.1021/acsmedchemlett.2c00027

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New Phosphorylating Agents for the Synthesis of Phosphatidylethanolamines 査読有り国際誌

Tsubaki K., Yamanaka T., Hisamitsu T., Shimooka H., Kitamura M., Okauchi T.

Synthesis ( Thieme ) 53 ( 20 ) 3827 - 3835 2021年10月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

The preparation of three novel phosphorylating agents and their application toward the synthesis of phosphatidylethanolamines is described. These reagents are stable to air and moisture, and phosphorylate glycerols in good yield. The experimental procedures using these phosphorylating agents are simple. Moreover, the appropriate reagent can be selected based on the desired functional groups of the targeted phosphatidylethanolamine.

DOI： 10.1055/a-1516-9893

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Building siRNAs with Cubes: Synthesis and Evaluation of Cubane-Modified siRNAs 査読有り

Hammill M.L.(Ontario Tech University), Salim L.(Ontario Tech University), Tsubaki K., Varley A.J.(Ontario Tech University), Kitamura M., Okauchi T., Desaulniers J.P.(Ontario Tech University)

ChemBioChem 22 ( 20 ) 2981 - 2985 2021年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

Cubane molecules hold great potential for medicinal chemistry applications due to their inherent stability and low toxicity. In this study, we report the synthesis of a cubane derivative phosphoramidite for the incorporation of cubane into small interfering RNAs (siRNAs). Synthetic siRNAs rely on chemical modifications to improve their pharmacokinetic profiles. However, they are still able to mediate sequence-specific gene silencing via the endogenous RNA interference pathway. We designed a library of siRNAs bearing cubane at different positions within the sense and antisense strands. All siRNAs showed excellent gene-silencing activity, with IC50 values ranging from 45.4 to 305 pM. Incorporating the cubane modification in both the sense and antisense strand led to viable duplexes with good biological activity. To the best of our knowledge, this is the first report of siRNAs bearing a cubane derivative within the backbone.

DOI： 10.1002/cbic.202100334

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Pyrrole Formation via Reactivity of η4-(Vinylketenimine)iron Complexes with Electron-Deficient Alkynes 査読有り国際誌

Tatsuo Okauchi, Akihiro Urakawa, Nagomi Tabuchi, Miten Arai, Tomoya Nakagawa, Taiga Ichimura, Hirokazu Shimooka, Mitsuru Kitamura

Organometallics ( American Chemical Society ) 40 ( 17 ) 2929 - 2933 2021年08月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

When electron-deficient alkynes reacted with η4-(vinylketenimine)iron complexes, pyrroles were produced. Pyrrole formation involved the [2 + 3] cycloaddition of alkyne to the ketenimine moiety, migration of the vinyl group, and decomplexation. Either alkynes bearing two electron-withdrawing groups, or terminal alkynes with an electron-withdrawing group reacted to generate pyrroles.

DOI： 10.1021/acs.organomet.1c00321

その他リンク： https://pubs.acs.org/doi/10.1021/acs.organomet.1c00321

PdBr<inf>2</inf>-Catalyzed Acetal Formation of Carbonyl Compounds Using Diazophenanthrenequinone: Utility of 9,10-Phenanthrenedioxyacetal 査読有り国際誌

Kitamura M., Fujimura R., Nishimura T., Takahashi S., Shimooka H., Okauchi T.

European Journal of Organic Chemistry 2020 ( 33 ) 5319 - 5322 2020年09月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim We developed a new acetalization method of ketones and aldehydes under non-acidic conditions using diazophenanthrenequinone and PdBr2. The formed acetals that have a phenanthrene skeleton withstand under mild acidic conditions. Removal of acetals was successfully proceeded under strong acidic or oxidation conditions using aqueous ceric ammonium nitrate (CAN) to afford corresponding ketones and aldehydes.

DOI： 10.1002/ejoc.202000315

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Synthesis and Evaluation of Neutral Phosphate Triester Backbone-Modified siRNAs 査読有り国際誌

Tsubaki K., Hammill M.L.(Ontario Tech University), Varley A.J.(Ontario Tech University), Kitamura M., Okauchi T., Desaulniers J.P.(Ontario Tech University)

ACS Medicinal Chemistry Letters 11 ( 7 ) 1457 - 1462 2020年07月

記述言語：英語掲載種別：研究論文（学術雑誌）

Copyright © 2020 American Chemical Society. Two unsymmetrical dinucleotide phosphate triesters were synthesized via transesterification from tris(2,2,2-trifluoroethyl) phosphate. The protected triesters were phosphytilated to generate phosphoramidites for solid-phase oligonucleotide synthesis. Neutral phenylethyl phosphate-modified short-interfering RNAs (siRNAs) were synthesized and evaluated for their gene-silencing ability, siRNA strand selection, and resistance to nucleases. These backbone-modified phosphate triester siRNAs offer many improvements compared to natural unmodified siRNAs.

DOI： 10.1021/acsmedchemlett.0c00232

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Rh(II)-catalyzed formal [3+3] cycloaddition of diazonaphthoquinones and propargyl alcohols: Synthesis of 2,3-dihydronaphtho-1,4-dioxin derivatives 査読有り国際誌

Kitamura M., Nishimura T., Otsuka K., Shimooka H., Okauchi T.

Tetrahedron Letters 61 ( 20 ) 2020年05月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 Elsevier Ltd A Rh(II)-catalyzed formal [3+3] cyclization of diazonaphthoquinones and propargyl alcohol is reported to afford 2,3-dihydro-1,4-benzodioxins. Various terminal propargyl alcohols react with diazonapthoquinone in the presence of Rh2(OAc)4 to give the corresponding dihydrodioxins in good to high yields. However, dihydrodioxins are not formed in the reaction of internal propargyl alcohols, and the O–H insertion product and 2,5-dihydrofurans are formed as the main product(s) depending on the terminal substituent. 2,3-Dihydro-1,4-benzodioxins are proposed to be formed via Rh(II)-catalyzed intermolecular oxonium ylide formation and subsequent 6-exo-dig cyclization with the internal alkynyl group.

DOI： 10.1016/j.tetlet.2020.151853

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九州工業大学工学部応用化学科の化学実験教育査読有り

中戸晃之, 竹中繁織, 岡内辰夫, 山村方人, 植田和茂

化学と教育 ( 公益社団法人日本化学会 ) 68 ( 3 ) 114 - 117 2020年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

<p>九州工業大学工学部応用化学科では，2年次前期より3年次後期にかけて，分析化学，物理化学，有機化学，化学工学・無機化学の順序で，学生実験を実施している。実験技術の習得に加え，エンジニアリングデザイン，コミュニケーション，チームワークなどの能力の涵養も目的としている。有機化学実験ではPBL（課題解決型学習）方式を取り入れており，学生アンケートや教員の実感では有効に機能していると考えられる。</p>

DOI： 10.20665/kakyoshi.68.3_114

その他リンク： https://ci.nii.ac.jp/naid/130007993107

Selective Transesterification of 2,2,2-Trifluoroethyl Phosphates: Synthesis of Mixed Unsymmetrical Phosphates 査読有り国際誌

Tsubaki K., Shimooka H., Kitamura M., Okauchi T.

Organic Letters 21 ( 23 ) 9779 - 9783 2019年12月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2019 American Chemical Society. A selective transesterification starting with tris(2,2,2-trifluoroethyl) phosphate has been developed. This method involves a three-step substitution for 2,2,2-trifluoroethoxy groups and enables the facile synthesis of mixed unsymmetric phosphate triesters from three different alcohols. The substitution of the trifluoroethoxy group at the phosphorus proceeds selectively in the presence of DBU or lithium alkoxides. This method can be applied for the preparation of phospholipids.

DOI： 10.1021/acs.orglett.9b04003

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85075667578&origin=inward

高校生のためのクロスカップリング実験（共著）

岡内辰夫,北村充

化学と教育 ( 日本化学会 ) 67 ( 3 ) 130 - 133 2019年03月

Pd-catalyzed cyclization of terminal alkynes using diazonaphthoquinones: Synthesis of naphtho[1,2-b]furans 査読有り国際誌

Takahashi S., Shimooka H., Okauchi T., Kitamura M.

Chemistry Letters 48 ( 1 ) 28 - 31 2019年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2019 The Chemical Society of Japan. Naphtho[1,2-b]furans were synthesized via a Pd-catalyzed reaction of diazonaphthoquinones and terminal alkynes in the presence of CuI and diisopropylamine. This method was then successfully applied to the synthesis of natural product, furomollugin.

DOI： 10.1246/cl.180803

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85059438494&origin=inward

高校生のためのクロスカップリング実験:—ノーベル化学賞の鈴木-宮浦クロスカップリングを題材に— 査読有り

岡内辰夫, 北村充

化学と教育 ( 公益社団法人日本化学会 ) 67 ( 3 ) 130 - 133 2019年01月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

<p>2010年，「有機合成におけるパラジウム触媒を用いたクロスカップリングの開発」に貢献した3人（Heck，根岸，鈴木）に，ノーベル化学賞が与えられた。そのうち2人が日本人であったため，マスコミで大きく取り上げられ，クロスカップリングという言葉が広く知られるようになった。受賞者の1人である北海道大学名誉教授の鈴木　章先生らのグループが開発した反応が，鈴木-宮浦クロスカップリングである。この反応は，有機ホウ素化合物と有機ハロゲン化合物に対して，パラジウム触媒を作用させることで炭素-炭素結合が形成するというものである。この反応は，我々の身の回りの医薬品，農薬，液晶材料，EL材料などの開発・量産化に大いに貢献している。</p>

DOI： 10.20665/kakyoshi.67.3_130

その他リンク： https://ci.nii.ac.jp/naid/130007804205

Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone 査読有り国際誌

Othman D., Otsuka K., Takahashi S., Selim K., El-Sayed M., Tantawy A., Okauchi T., Kitamura M.

Synlett 29 ( 4 ) 457 - 462 2018年03月

記述言語：英語掲載種別：研究論文（学術雑誌）

© Georg Thieme Verlag Stuttgart New York. The first total synthesis of (±)-eleutherol and eleuthoside A, the natural cytotoxic substances extracted from medicinal Indonesian plant, is described. First, the synthesis of (±)-eleutherol has been accomplished in nine steps starting from bromo methoxy aldehyde with the aid of diazo-transfer chemistry approach. Second, a metal-catalyzed intramolecular cyclization reaction of the corresponding diazonaphthoquinone led to the desired eleuotherol, which served as a precursor to eleuthoside A. Then, several glycosidation routes, using different glucosyl donors, were experimented to reach effective O-glycosidation of eleutherol. The only successful strategy involved Koenigs-Knorr glycosidation using peracetyl glycosyl bromide in the presence of Ag 2 O and quinoline. This strategy furnished our desired acetylated glycoside of β-configuration, regioselectively. Finally, deacetylation and successive separation of diastereomers were conducted to give eleuthoside A.

DOI： 10.1055/s-0036-1589118

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Synthesis of 1,2-naphthalenediol derivatives by Rh-catalyzed intermolecular O[sbnd]H insertion reaction of 1,2-diazonaphthoquinones with water and alcohols 査読有り国際誌

Kitamura M., Otsuka K., Takahashi S., Okauchi T.

Tetrahedron Letters 58 ( 36 ) 3508 - 3511 2017年09月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2017 Elsevier Ltd Rh(II)-catalyzed O[sbnd]H insertion reaction of diazonaphthoquinones with water or alocohols proceeded to yield 1,2-naphthalenediol derivatives.

DOI： 10.1016/j.tetlet.2017.07.084

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Synthesis of (±)-myo-inositol 4-methylenephosphonate via Rh-Catalyzed hydrogenation of vinylphosphonate 査読有り国際誌

Tatsuo Okauchi, Shuya Nakamura, Kouta Tsubaki, Momoko Asakawa, Mitsuru Kitamura

Carbohydrate Research 448 24 - 27 2017年08月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

Phosphatidylinositol phosphate (PIP) synthetase is a promising target for the development of new anti-mycobacterium compounds. We previously reported that myo-inositol 1-methylenephosphonate showed inhibitory activity against PIP synthetase. Herein, we report the synthesis of unprotected myo-inositol 4-methylenephosphonate, a constitutional isomer of myo-inositol 1-methylenephosphonate and found that the stereoselective hydrogenation of vinylphosphonate proceeded via Rh catalysis.

DOI： 10.1016/j.carres.2017.05.018

その他リンク： http://www.sciencedirect.com/science/article/pii/S0008621517303269

Synthesis, characterization and air stable semiconductor properties of thiophene-condensed pyrene derivatives 査読有り

Moriguchi T., Higashi M., Yakeya D., Jalli V., Tsuge A., Okauchi T., Nagamatsu S., Takashima W.

Journal of Molecular Structure 1127 413 - 418 2017年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2016 Elsevier B.V.New and simple polyaromatic compounds containing two thiophene rings were prepared via photo-cyclization and their structural and photophysical properties were evaluated via 1H NMR spectroscopy and X-ray crystallographic analysis. On the basis of X-ray analysis, it was determined that the molecular structure of the compound was highly strained and that they contain two hetero [4] helicene moieties. The compounds were investigated as active layer in p-type organic field-effect transistors (p-OFET) in top contact type devices. Notably, the compound containing two thiophene components exhibited very stable p-type semiconducting behavior in moist air.

DOI： 10.1016/j.molstruc.2016.07.104

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Molecular structures of n-type semiconducting material 2,5-difluoro-1,4-phenylene-3,3′-bis{2-[(4-trifluoromethyl)phenyl]acrylonitrile} and its photo dimerization product 査読有り

Moriguchi T., Kitou N., Jalli V., Yoza K., Nagamatsu S., Okauchi T., Tsuge A., Takashima W.

Journal of Molecular Structure 1118 372 - 377 2016年08月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2016 Elsevier B.V. All rights reserved.The absolute molecular structure of air stable n-type semiconducting material 2,5-difluoro-1,4-phenylene-3,3′-bis{2-[(4-trifluoromethyl)phenyl]acrylonitrile} was determined by using twin crystal treatment X-ray diffraction analysis. The compound was readily dimerized in solution via irradiating of UV or Sun light. The exact molecular structure of the dimer also determined by X-ray analysis.

DOI： 10.1016/j.molstruc.2016.04.035

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Axially Chiral Bifunctional 8,8′-Biquinolyl: Synthesis of 7,7′-Dihydroxymethyl-8,8′-biquinolyl via Pd-Catalyzed Double C-H Oxidation of 7,7′-Dimethyl-8,8′-biquinolyl 査読有り

Kitamura M., Fukuma H., Kobayashi M., Okayama S., Okauchi T.

Journal of Organic Chemistry 81 ( 9 ) 3956 - 3960 2016年05月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2016 American Chemical Society.Bifunctional C2-symmetric 7,7′-dihydroxymethyl-8,8′-biquinolyl (2) was synthesized in short steps via (i) Cu/Pd-catalyzed homo coupling of 7-methyl-8-bromoquinoline and (ii) Pd(II)-catalyzed double C-H oxidation. Axial chirality of 2 and its synthetic precursor 7,7′-dimethyl-8,8′-biquinolyl (3) is stable. Optically active 2 was obtained through separation of racemic 2 by chiral column HPLC or Pd(II)-catalyzed double C-H oxidation of optically active 3. The absolute stereochemistry of enantiomers of 2 and 3 was determined using the exciton chirality method.

DOI： 10.1021/acs.joc.6b00534

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Synthesis, structure, and reaction of chiral 2-azidoimidazolinium salts: (7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate 査読有り

Kitamura M., Ishikawa A., Okauchi T.

Tetrahedron Letters 57 ( 16 ) 1794 - 1797 2016年04月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2016 Published by Elsevier Ltd.Two chiral 2-azidoimidazolinium salts [(7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate (2) and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate (3)] were synthesized, and their structures were determined by X-ray single crystal structural analysis. Migratory amidation reaction of enol silyl ether with 3 proceeded, but good diastereoselectivity was not observed in the reaction.

DOI： 10.1016/j.tetlet.2016.03.036

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Pinpoint-fluorinated phenanthrene synthesis based on C-F bond activation of difluoroalkenes 査読有り

K. Fuchibe, T. Morikawa, R. Ueda, T. Okauchi, J. Ichikawa

Journal of Fluorine Chemistry 179 106 - 115 2015年11月

Rh-Catalyzed Cyclization of 3-Aryloxycarbonyldiazonaphthoquinones for the Synthesis of beta-Phenylnaphthalene Lactones and Formal Synthesis of Pradimicinone 査読有り

M. Kitamura, S. Takahashi, T. Okauchi

The Journal of Organic Chemistry 80 ( 16 ) 8406 - 8416 2015年08月

Thermodynamics and kinetic studies in the binding interaction of cyclic naphthalene diimide derivatives with double stranded DNAs 査読有り

M. M. Islam, S. Fujii, S. Sato, T. Okauchi, S. Takenaka

Bioorganic & Medicinal Chemistry 23 ( 15 ) 4769 - 4776 2015年08月

Synthesis of Diazonaphthoquinones from Naphthols by Diazo-Transfer Reaction 査読有り

M. Kitamura, R. Sakata, N. Tashiro, A. Ikegami, T. Okauchi

Bulletin of the Chemical Society of Japan 88 ( 6 ) 824 - 833 2015年06月

A Selective G-Quadruplex DNA-Stabilizing Ligand Based on a Cyclic Naphthalene Diimide Derivative 査読有り

M. M. Islam, S. Fujii, S. Sato, T. Okauchi, S. Takenaka

Molecules 20 ( 6 ) 10963 - 10979 2015年06月

Unprecedented formation of hapto4-(vinylketene)iron complexes from hapto4-(diene)iron complexes and aromatic compounds in the presence of a Lewis acid 査読有り

Tatsuo Okauchi, Naoki Sata, Akihiro Urakawa, Mitsuru Kitamura

Chemical Communications 51 ( 40 ) 8454 - 8456 2015年05月

Long-Term Air-Stable n-Channel Organic Thin-Film Transistors Using 2,5-Difluoro-1,4-phenylene-bis{2-[4-(trifluoromethyl)phenyl]acrylonitrile} 査読有り

Shuichi Nagamatsu, Shinya Oku, Kouji Kuramoto, Tetsuji Moriguchi, Wataru Takashima, Tatsuo Okauchi, Shuzi Hayase

ACS Applied Materials & Interfaces 6 3847 - 3852 2014年03月

Pd(OAc)2-Catalyzed Macrocyclization of 1,2-Diazonaphthoquinones with Cyclic Ethers 査読有り

Mitsuru Kitamura, Masato Kisanuki, Koichi Kanemura, Tatsuo Okauchi

Organic Letters 16 ( 6 ) 1554 - 1557 2014年03月

A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate 査読有り

Mitsuru Kitamura, So Kato, Masakazu Yano, Norifumi Tashiro, Yuichiro Shiratake, Mitsuyoshi Sandoa, Tatsuo Okauchi

Organic & Biomolecular Chemistry 12 ( 25 ) 4397 - 4406 2014年01月

Rhodium-Catalyzed Reaction of Diazonaphthoquinones and Enol Ethers: Synthesis of Dihydronaphthofuran Derivatives and alpha-Naphthyl Esters 査読有り

Mitsuru Kitamura, Keiichiro Araki, Hiroki Matsuzaki, Tatsuo Okauchi

European Journal of Organic Chemistry 2013 ( 23 ) 5045 - 5049 2013年08月

Synthesis of alpha-Arylcarboxylic Acid Amides from Silyl Enol Ether via Migratory Amidation with 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate 査読有り

Mitsuru Kitamura, Kento Murakami, Yuichiro Shiratake, Tatsuo Okauchi

Chemistry Letters 42 ( 7 ) 691 - 693 2013年07月

Studies of inositol 1-phosphate analogues as inhibitors of the phosphatidylinositol phosphate synthase in mycobacteria 査読有り

H. Morii, T. Okauchi, H. Nomiya, M. Ogawa, K. Fukuda, H. Taniguchi

The Journal of Biochemistry 153 ( 3 ) 257 - 266 2013年03月

Cu(OAc)2-Mediated Cross-Coupling Reaction of Benzophenone N,N,N-Trimethylhydrazonium Salts and Aryl Boronic Acids 査読有り

Mitsuru Kitamura, Yu Tokuda, Norifumi Tashiro, Tatsuo Okauchi

Australian Journal of Chemistry 65 ( 12 ) 1687 - 1690 2012年11月

Direct Synthesis of Organic Azides from Alcohols Using 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate 査読有り

Mitsuru Kitamura, Tatsuya Koga, Masakazu Yano, Tatsuo Okauchi

Synlett ( 9 ) 1335 - 1338 2012年06月

Synthesis of 1,2-Naphthalenediol Diacetates by Rhodium(II)-Catalyzed Reaction of 1,2-Diazonaphthoquinones with Acetic Anhydride 査読有り

Mitsuru Kitamura, Masato Kisanuki, Tatsuo Okauchi

European Journal of Organic Chemistry ( 5 ) 905 - 907 2012年02月

Pd(II)-catalyzed Formal O-H Insertion Reactions of Diazonaphthoquinones to Acetic Acid: Synthesis of 1,2-Naphthalenediol Derivatives "jointly worked" 査読有り

Mitsuru Kitamura, Masato Kisanuki, Rie Sakata, Tatsuo Okauchi

Chemistry Letters 40 ( 10 ) 1129 - 1131 2011年10月

Synthesis of pi-Conjugated Copolymers Composed of Benzo[2,1,3]thiadiazole and Thiophene Units Bearing Various Alkyl Groups and Their Application to Photovoltaic Cells "jointly worked" 査読有り

Lee, Kwang-Hoi)Ho-Jin Lee, K, Kouji Kuramoto, Yohei Tanaka, Kazuhide Morino, Atsushi Sudo, Tatsuo Okauchi, Akihiko Tsuge, Takeshi Endo

Journal of Polymer Science Part A-Polymer Chemistry 49 ( 16 ) 3543 - 3549 2011年08月

Synthesis of π-conjugated copolymers composed of benzo[2,1,3]thiadiazole and thiophene units bearing various alkyl groups and their application to photovoltaic cells 査読有り

Lee K., Lee H., Kuramoto K., Tanaka Y., Morino K., Sudo A., Okauchi T., Tsuge A., Endo T.

Journal of Polymer Science, Part A: Polymer Chemistry 49 ( 16 ) 3543 - 3549 2011年08月

記述言語：英語掲載種別：研究論文（学術雑誌）

π-Conjugated polymers, PTOTBT, PTEHTBT, and PTt-BTBT, composed of benzothiadiazole as an electron accepting unit and terthiophene as an electron donating unit in the backbone were prepared. PTOTBT, PTEHTBT, and PTt-BTBT contained side chain groups of n-octyl, 2-ethylhexyl, and t-butyl groups, respectively. Solubility, optical and thermal properties of the polymers showed strong dependences on their side chain groups. PTEHTBT having 2-ethylhexyl groups in the side chain exhibited absorption maximum (Imax) at longer wavelength (565 nm) than PTOTBT (534 nm) and PTt-BTBT (495 nm). PTOTBT showed higher thermal stability than the others. The prepared polymers were employed to polymer solar cells (PSCs) with a configuration of ITO/PEDOT-PSS/polymer: PC61BH/LiF/Al. Power conversion efficiency of the PSC-based on PTEHTBT was 1.32%. © 2011 Wiley Periodicals, Inc.

DOI： 10.1002/pola.24790

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Synthesis of alpha,alpha-diarylacetamides from benzyl aryl ketones using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate "jointly worked" 査読有り

Mitsuru Kitamura, Satoshi Miyagawa, Tatsuo Okauchi

Tetrahedron Letters 52 ( 24 ) 3158 - 3161 2011年06月

Synthesis of α,α-diarylacetamides from benzyl aryl ketones using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate 査読有り

Kitamura M., Miyagawa S., Okauchi T.

Tetrahedron Letters 52 ( 24 ) 3158 - 3161 2011年06月

記述言語：英語掲載種別：研究論文（学術雑誌）

Benzyl aryl ketones reacted with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP, 1) to give migratory amidated compounds, which were transformed into the corresponding diarylacetamides by treating with LiAlH 4. © 2011 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2011.04.042

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Palladium-catalyzed cross-coupling reactions of 2-diazonaphthoquinones with arylboronic acids "jointly worked" 査読有り

Mitsuru Kitamura, Rie Sakata, Tatsuo Okauchi

Tetrahedron Letters 52 ( 16 ) 1931 - 1933 2011年04月

2-Azido-1,3-dimethylimidazolinium Salts: Efficient Diazo-Transfer Reagents for 1,3-Dicarbonyl Compounds "jointly worked" 査読有り

Mitsuru Kitamura, Norifumi Tashiro, Satoshi Miyagawa, Tatsuo Okauchi

Synthesis ( 7 ) 1037 - 1044 2011年04月

Synthesis of Isoindole Derivatives by Palladium-Catalyzed Domino Reaction of (2-Alkynyl)phenylketone O-Pentafluorobenzoyloximes "jointly worked" 査読有り

Mitsuru Kitamura, Yohei Moriyasu, Tatsuo Okauchi

Synlett ( 5 ) 643 - 646 2011年03月

Polythiophenes Bearing Electron-Withdrawing Groups in the Side Chain and Their Application to Bulk Heterojunction Solar Cells"jointly worked" 査読有り

Kwang-Hoi Lee, Ho-Jin Lee, Kouji Kuramoto, Yohei Tanaka, Kazuhide Morino, Atsushi Sudo, Tatsuo Okauchi, Akihiko Tsuge, Takeshi Endo

Journal of Polymer Science Part A-Polymer Chemistry 49 ( 1 ) 234 - 241 2011年01月

Facile Preparation of Aryl Sulfides Using Palladium Catalysis under Mild Conditions "jointly worked" 査読有り

Tatsuo Okauchi, Kouji Kuramoto, Mitsuru Kitamura

Synlett ( 19 ) 2891 - 2894 2010年12月

Synthesis of Diazonaphthoquinones from Naphthols by Diazo-Transfer Reaction with 2-Azido-1,3-dimethylimidazolinium Chloride "jointly worked" 査読有り

Mitsuru Kitamura, Norifumi Tashiro, Rie Sakata, Tatsuo Okauchi

Synlett ( 16 ) 2503 - 2505 2010年10月

Low-valent zirconocene-mediated cyclization of gamma,delta-unsaturated oximes "jointly worked" 査読有り

Mitsuru Kitamura, Yuki Shintaku, Daisuke Kudo, Tatsuo Okauchi

Tetrahedron Letters 51 ( 37 ) 4890 - 4893 2010年09月

Enantioselective Synthesis of alpha-Benzylalanine Using trans-3,4-Dihydro-3,4-diaryldibenzo[c,g]phenanthrene-3,4-diols "jointly worked" 査読有り

Mitsuru Kitamura, Daisuke Kitahara, Tatsuo Okauchi

Synlett ( 14 ) 2097 - 2100 2010年09月

Direct Synthesis of Acyl Azides from Carboxylic Acids Using 2-Azido-1,3-dimethylimidazolinium Chloride "jointly worked" 査読有り

Mitsuru Kitamura, Norifumi Tashiro, Yusuke Takamoto, Tatsuo Okauchi

Chemistry Letters 39 ( 7 ) 732 - 733 2010年07月

2-azido-1,3-dimethylimidazolinium chloride: An efficient diazo transfer reagent for 1,3-dicarbonyl compounds 査読有り

Kitamura M., Tashiro N., Okauchi T.

Synlett ( 18 ) 2943 - 2944 2009年12月

記述言語：英語掲載種別：研究論文（学術雑誌）

Diazo transfer from 2-azido-1,3-dimethylimidazolinium chloride to 1,3-dicarbonyl compounds has been developed. The -reaction proceeds under mild conditions to give 2-diazo-1,3-dicarbonyl compounds in high yields, which are easily isolated because the by-products are highly soluble in water. © Georg Thieme Verlag Stuttgart.

DOI： 10.1055/s-0029-1218269

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2-Azido-1,3-dimethylimidazolinium Chloride: An Efficient Diazo Transfer Reagent for 1,3-Dicarbonyl Compounds "jointly worked" 査読有り

Mitsuru Kitamura, Norifumi Tashiro, Tatsuo Okauchi

Synlett ( 18 ) 2943 - 2944 2009年11月

A Steady Operation of n-Type Organic Thin-Film Transistors with Cyano-Substituted Distyrylbenzene Derivative "jointly worked" 査読有り

Shuichi Nagamatsu, Tetsuji Moriguchi, Toshiya Nagase, Shinya Oku, Kouji Kuramoto, Wataru Takashima, Tatsuo Okauchi, Katsuhiro Mizoguchi, Shuji Hayase, Keiichi Kaneto

Applied Physics Express 2 ( 10 ) 101502 2009年10月

A steady operation of n-type organic thin-film transistors with cyano-substituted distyrylbenzene derivative 査読有り

Nagamatsu S., Moriguchi T., Nagase T., Oku S., Kuramoto K., Takashima W., Okauchi T., Mizoguchi K., Hayase S., Kaneto K.

Applied Physics Express 2 ( 10 ) 2009年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

A novel n-type organic semiconductor, cyano-substituted distyrylbenzene derivative, 1,4-bis{2-[4-(trifluoromethyl)phenyl]acrylonitorile}-benzene, was synthesized by Knoevenagel condensation with aldehyde and acetonitrile derivatives. Fabricated thin-film transistors (TFTs) exhibited high electron field-effect mobility of 10-2-10-1 cm2 V-1 s-1, on/off current ratio of 6 - 105. Hysteresis-free n-type transport © 2009 The Japan Society of Applied Physics.

DOI： 10.1143/APEX.2.101502

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Preparation of colloidal silica grafted with iron(0) carbonyl complex/polymer and formation of colloidal crystals in organic solvents 査読有り

Nakano M., Mouri E., Karakawa H., Okauchi T., Yoshinaga K., Nakai A.

Polymer Preprints, Japan 55 ( 1 ) 2006年10月

記述言語：英語掲載種別：研究論文（国際会議プロシーディングス）

Chemical modification of colloidal silica with poly(methyl methacrylate) containing tricarbonyliron(0) moiety, and colloidal crystallization in organic solvents were investigated. The polymer grafting to silica was carried out in 1,2-dimethoxyethane under refluxing using the polymer-silane, prepared by condensation of 3-aminopropyltriethoxysilane and carboxyl-terminated copolymer synthesized by radical polymerization of iron(0)tricarbony1(4,4-dimethyl-1,2- cyclohexadieny1) acrylate or methacrylate and methyl methacrylate using an initiator of 4,4′-azobis(4-cyanovaleric acid) in tetrahydrofuran. The polymer-modified silica formed relatively stable colloidal crystals in acetone or N,N-dimethylformamide.

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Chlamydocin analogs bearing carbonyl group as possible ligand toward zinc atom in histone deacetylases 査読有り

M. P.I. Bhuiyan,T. Kato,T. Okauchi,N. Nishino,S. Maeda,T. G. Nishino,M. Yoshida

Bioorganic & Medicinal Chemistry 14 ( 10 ) 3438 - 3446 2006年05月

Facile Synthesis of Modified Cyclic Imino Acids with Methyl and Hydroxyl Groups 査読有り

BHUIYAN Mohammed P. I., WATANABE Louis A., IKEDA Satoshi, JUNG An-Na, KATO Tamaki, OKAUCHI Tatsuo, NISHINO Norikazu

Peptide science : proceedings of the ... Japanese Peptide Symposium 2005 15 - 18 2006年03月

Generation of alpha-phosphonovinyl radicals and development of a new route to highly functionalized vinylphosphonates and vinylphosphonate-incorporated carbocyclic or heterocyclic compounds via a radical trapping sequence 査読有り

Takafumi Ageno,Tatsuo Okauchi,Toru Minami,Masaru Ishida

Organic and Biomolecular Chemistry 3 ( 5 ) 924 - 931 2005年04月

Generation of α-phosphonovinyl radicals and development of a new route to highly functionalized vinylphosphonates and vinylphosphonate- incorporated carbocyclic or heterocyclic compounds via a radical trapping sequence 査読有り

Ageno T., Okauchi T., Minami T., Ishida M.

Organic and Biomolecular Chemistry 3 ( 5 ) 924 - 931 2005年03月

記述言語：英語掲載種別：研究論文（学術雑誌）

The first direct generation of synthetically useful α-phosphonovinyl radicals was achieved by treatment of α-phosphonovinyl halides with a tributyltin radical. The α-phosphonovinyl radicals 2a-d were trapped with electron-rich olefins and an electron-deficient olefin to produce α-functionalized vinylphosphonates 3a-f in 16-55% yields. The α-phosphonovinyl radicals 7e-g containing the YCH2CH=CH 2 (Y = O, CH2, S) substituent at the β-position afforded mixtures of 5-exo and 6-endo cyclization products, 5e-g and 6e-g, in good yields. The 5-exo/6-endo product ratios increase in the following order of the β-substituent: OCH2CH=CH2 > CH 2CH2CH=CH2 > SCH2CH=CH 2. The effects of the β-substituents upon the cyclization reaction were discussed. Radical cyclization of α-phosphonovinyl radicals bearing functional groups such as geranyloxy, geranylthio, and (2-cyclohexen-l-yl)thio groups at the β-position afforded 5-exo, 5-exo and 6-endo, and cis-fused-5,6-ring cyclization products incorporating an α,β-unsaturated phosphonate unit within the ring, respectively, in good yields. The β-phosphonovinyl radical 20 underwent tandem radical cyclization-radical cyclization to produce a mixture of two isomeric bicyclo[4.3.0]nonenes including a vinylphosphonate moiety in high yield. © The Royal Society of Chemistry 2005.

DOI： 10.1039/b416394j

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Vinyl-and arylphosphorus derivatives 査読有り

Minami T., Okauchi T.

Comprehensive Organic Functional Group Transformations II 2 853 - 907 2004年12月

Acid-promoted reaction of trimethylsilylketene bis(ethylthio)acetal with imines. Synthesis of γ,γ-bis(ethylthio)allylamines 査読有り

Yahiro S., Shibata K., Saito T., Okauchi T., Minami T.

Journal of Organic Chemistry 68 ( 12 ) 4947 - 4950 2003年06月

記述言語：英語掲載種別：研究論文（学術雑誌）

Acid-catalyzed reaction of silylketene dithioacetal 1 with iminium salts or imines 3b,d-h gave the corresponding γ,γ-bis(ethylthio)allylamines 2a-h or 5b,d-h in generally high yields. Similar reactions of 1 with (salicylidene)-amines 6a-e afforded 4-amino-2,2-bis(ethylthio)chromans 8a-e in good to moderate yields.

DOI： 10.1021/jo020748v

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New synthesis of gem-bis(phosphono)ethylenes and their applications 査読有り

Inoue S., Okauchi T., Minami T.

Synthesis ( 13 ) 1971 - 1976 2003年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

Palladium-catalyzed cross-coupling reaction of α-phosphonovinyl nonafluorobutanesulfonates (nonaflates) 1 with dialkyl phosphites gave versatile intermediate reagents, gembis(phosphono)ethylenes 2a-d in 35-93% yields. The reaction of bis(diethylphosphono)ethylene (2a) with tribromomethyllithium to give the Michael adduct 3 was followed by treatment with potassium hydride to form 1,1-dibromo-2,2-bis(phosphono)cyclopropane 4 in 68% yield. The reaction of 2a with [N-(p-toluenesulfonyl)- or N-(methanesulfonyl)imino]phenyliodinane produced the corresponding 1-sulfonyl-2,2-bis(phosphono)aziridines 5a,b in 54-75% yields. Treatment of 2a with sodium or potassium imidazole and a halogenating agent led to [1-halo-2-(1-imidazolyl)ethyl]-1,1-bisphosphonates 7a,b (halogen = Cl, F) in 73-47% yields. Similar reaction using 3-lithiopyridine and a halogenating agent afforded [1-halo-2-(3-pyridyl)ethyl]-1,1-bisphosphonates 8a,b in 83-85% yields.

DOI： 10.1055/s-2003-41002

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The first synthesis of phosphonoacrolein 査読有り

Arimori S., Kouno R., Okauchi T., Minami T.

Phosphorus, Sulfur and Silicon and Related Elements 177 ( 8-9 ) 1953 - 1954 2002年11月

The first synthesis of phosphonoacrolein. Application to Diels-Alder reaction as heterodiene 査読有り

Arimori S., Kouno R., Okauchi T., Minami T.

Journal of Organic Chemistry 67 ( 21 ) 7303 - 7308 2002年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

The first synthesis of phosphonoacrolein 3 was made in quantitative yield by acidic treatment of β-ethoxy-α-(methoxymethyl)vinylphosphonate 2, derived from a β-ethoxy-α-phosphonovinyl anion and MOMCl. The phosphonoacrolein 3 easily underwent a hetero-Diels-Alder reaction with electron-rich alkenes 4a-f or alkynes 9a-c under mild conditions, and phosphono-substituted pyrans 5a-d, 6e,f or pyranopyrans 11a-c were obtained in good to excellent yields. The reaction of 3 with cyclopentadiene and cyclohexadiene led to mixtures of [2 + 4] and [4 + 2] cycloadducts 7a, 8a and 7b, 8b in modest yields. The cycloaddition reaction between 3 and pyranopyran 13 or dibromocarbene and 13 resulted in [4 + 2] or [2 + 1] cycloadducts 14 or 15 in good yields.

DOI： 10.1021/jo020403c

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Synthesis and biological evaluation of N-(7-indolyl)-3-pyridinesulfonamide derivatives as potent antitumor agents 査読有り

Owa T., Yoshino H., Okauchi T., Okabe T., Ozawa Y., Hata Sugi N., Yoshimatsu K., Nagasu T., Koyanagi N., Kitoh K.

Bioorganic and Medicinal Chemistry Letters 12 ( 16 ) 2097 - 2100 2002年08月

記述言語：英語掲載種別：研究論文（学術雑誌）

We herein report the synthesis and antitumor activity of E7070 analogues containing a 3-pyridinesulfonamide moiety. E7070 was selected from our sulfonamide-based compound collections, currently undergoing Phase II clinical trials because of its tolerable toxicity profile and some antitumor responses in the Phase I setting. Of the analogues examined, ER-35745, a 6-amino-3-pyridinesulfonamide derivative, demonstrated significant oral efficacy against the HCT116 human colon carcinoma xenograft in nude mice. © 2002 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0960-894X(02)00376-1

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Synthesis and Biological Evaluation of N-(7-Indolyl)-3-Phridinesulfonamide Derivatives as Potent Antitumor Agents 査読有り

岡内　辰夫

Biolrganic & Medicinal Chemistry Letters 12 ( 16 ) 2097 - 2100 2002年04月

The First Synthesis of Phosphonoacrolein. Application to Diels-Alder Reaction as Heterodiene 査読有り

岡内　辰夫

The Journal of Organic Chemistr 67 ( 21 ) 7303 - 7308 2002年04月

Synthesis and Biological Evaluation of N-(7-Indolyl)-3-Phridinesulfonamide Derivatives as Potent Antitumor Agents 査読有り

岡内　辰夫

Biolrganic & Medicinal Chemistry Letters 12 ( 16 ) 2097 - 2100 2002年04月

The First Synthesis of Phosphonoacrolein. Application to Diels-Alder Reaction as Heterodiene 査読有り

岡内　辰夫

The Journal of Organic Chemistry 67 ( 21 ) 7303 - 7308 2002年04月

Regioselective proton abstraction and 1,3-migration of a phosphorus group in 1,3-dienes by iron coordination: A new method for the synthesis of α-phosphono-α,β-unsaturated ketones [17] 査読有り

Okauchi T., Teshima T., Hayashi K., Suetsugu N., Minami T.

Journal of the American Chemical Society 123 ( 48 ) 12117 - 12118 2001年12月

Lewis acid-promoted deoxygenative di[β,β-bis(ethylthio)]vinylation of aldehydes with trimethylsilylketene bis(ethylthio)acetal 査読有り

Okauchi T., Tanaka T., Minami T.

Journal of Organic Chemistry 66 ( 11 ) 3924 - 3929 2001年06月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

Silylketene dithioacetal 1 reacted with aldehydes 2a-o, 14, or cinnamaldehyde (11) in the presence of Lewis acid to give deoxygenative divinylation products, 3-substituted 1,4-pentadienes 3a-o, 15, or 5-phenyl-1,3,6-heptatriene 13b, in good to moderate yields. Similar reaction with 2-aminobenzaldehyde (16) or salicylaldehyde (17) produced quinoline 19 or chroman 20 in 40-58% yield. Treatment of 1 with α-diketones 22a-c or α-ketoester 24 led to tetrasubstituted furans 23a-c or allylic alcohol 25, respectively, in rather low yields. The formation mechanisms of these products are discussed.

DOI： 10.1021/jo010007e

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Intramolecular Cyclizations of ο-substituted β,β-Difluorostyrenes: Synthesis of 3-Fluorinated Isochromenes and Isotheiochromenes 査読有り

Wada Yukinori, Ichikawa Junji, Katsume Tadayuki, NOHIRO Tomoko, OKAUCHI Tatsuo, MINAMI Toru

Bulletin of the Chemical Society of Japan ( Chemical Society of Japan ) 74 ( 5 ) 971 - 977 2001年05月

Regioselective Proton Abstraction and 1.3-Migration of a Phosphorus Group in 1.3-Dienes by Iron Coordination: A New Method for the Synthesis of α-Phosphono-α,β-Unsaturated Ketores. 査読有り

岡内　辰夫

Journal of the American Chemical Society 123 ( 48 ) 12117 - 12118 2001年04月

Intramolecular Cyclizations of o-Substituted β, β-Difluorostyrenes : Synthesis of 3-Fluorinated Isochromenes and Isothiochromenes 査読有り

岡内　辰夫

Bulletin of the Chemical Society of Japan 74 ( 5 ) 971 - 977 2001年04月

Regioselective Proton Abstraction and 1.3-Migration of a Phosphorus Group in 1.3-Dienes by Iron Coordination: A New Method for the Synthesis of α-Phosphono-α,β-Unsaturated Ketores. 査読有り

岡内　辰夫

Journal of the American Chemical Society 123 ( 48 ) 12117 - 12118 2001年04月

α-Phosphonovinyl Carbanions in Organic Synthesis 査読有り

岡内　辰夫

Synthesis ( 3 ) 349 - 357 2001年04月

Lewis Acid-promoted Deoxygenative Di[β, β-bis(ethylthio)]vinylation of Aldehydes with Trimethylsilylketene Bis(ethylthio)acetal 査読有り

岡内　辰夫

The Journal of Organic Chemistry 66 ( 11 ) 3924 - 3929 2001年04月

Regioselective Nucleophilic Additions to Cross-Conjugated Dienone System Bearing β-Fluorine : A Versatile Approach to Highly Substituted 2-Cyclopentenones 査読有り

岡内　辰夫

Organic Letters 3 ( 15 ) 2345 - 2348 2001年04月

The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups: Syntheses of ring-fluorinated dihydroheteroaromatics 査読有り

Ichikawa J., Fujiwara M., Wada Y., Okauchi T., Minami T.

Chemical Communications ( 19 ) 1887 - 1888 2000年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

Gem-Difluoroolefins bearing homoallylic tosylamido, hydroxy, or mercapto groups undergo intramolecular nucleophilic substitution of the nitrogen, oxygen, or sulfur with loss of fluorine via a 5-endo-trig process, leading to 2-fluoro-2-pyrrolines, 5-fluoro-2,3-dihydrofurans, or -thiophenes in high yields.

DOI： 10.1039/b004978f

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Synthesis and synthetic application of α-formylvinylphosphonates. Facile synthesis of phosphono-substituted heterocyclic compounds 査読有り

Kouno R., Tsubota T., Okauchi T., Minami T.

Journal of Organic Chemistry 65 ( 14 ) 4326 - 4332 2000年07月

記述言語：英語掲載種別：研究論文（学術雑誌）

The β-ethoxy-α-phosphonovinyl anion, generated from β- (ethoxy)vinylphosphonate 1 and LDA, reacted with aldehydes and ketones or phenyl isocyanate to give the corresponding allylic alcohols 2a-m or 1,3- diphenyl-5-phosphonouracil 4 in good or moderate yields. Treatment of the alcohols 2a-d,g,h,j with trifluoroacetic acid led to α- formylvinylphosphonates 5a-d,g,h,j in excellent yields. Synthetic application of the α-formylvinylphosphonates 5a-d,g,h to phosphono-substituted heterocyclic compounds was studied.

DOI： 10.1021/jo000149t

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A focused compound library of novel N-(7-indolyl)benzenesulfonamides for the discovery of potent cell cycle inhibitors 査読有り

Owa T., Okauchi T., Yoshimatsu K., Sugi N., Ozawa Y., Nagasu T., Koyanagi N., Okabe T., Kitoh K., Yoshino H.

Bioorganic and Medicinal Chemistry Letters 10 ( 11 ) 1223 - 1226 2000年06月

記述言語：英語掲載種別：研究論文（学術雑誌）

A series of compounds containing an N-(7-indolyl)benzenesulfonamide pharmacophore was synthesized and evaluated as a potential antitumor agent. Cell cycle analysis with P388 murine leukemia cells revealed that there were two different classes of potent cell cycle inhibitors; one disrupted mitosis and the other caused G1 accumulation. Herein described is the SAR summary of the substituent patterns on this pharmacophore template. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0960-894X(00)00219-5

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A general method for acylation of ndoles at the 3-position with Acyl chlorides in the presence of dialkylaluminum chloride 査読有り

Okauchi T., Itonaga M., Minami T., Takashi O., Kitoh K., Yoshino H.

Organic Letters 2 ( 10 ) 1485 - 1487 2000年05月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

(Matrix presented) Indoles are selectively acylated at the 3-position in high yields on treatment with a wide variety of acyl chlorides in CH2CI2 in the presence of diethylaluminum chloride or dimethylaluminum chloride. The reaction proceeds under mild conditions and is applicable to indoles bearing various functional groups without NH protection.

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Asymmetric allylic alkylation of cycloalkenediol diacetates using a chiral phosphine ligand bearing a carboxyl group 査読有り

Okauchi T., Fujita K., Ohtaguro T., Ohshima S., Minami T.

Tetrahedron Asymmetry 11 ( 6 ) 1397 - 1403 2000年04月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

Asymmetric induction in the allylic alkylation of cycloalkenediol diacetates was performed using a chiral alkylphosphine ligand bearing a carboxyl group, 3-(diphenylphosphino)butanoic acid. An increase in enantiomeric excess of the monoalkylated products of cis-cycloalkenediol diacetates was observed through a sequential asymmetric allylic alkylation- kinetic resolution process. (C) 2000 Elsevier Science Ltd.

DOI： 10.1016/S0957-4166(00)00080-X

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Asymmetric Allylic Alkylation of Cycloalkenediol Diacetates Using a Chiral Phosphine Ligand Bearing a Carbonyl Group 査読有り

岡内　辰夫

Tetrahedron : Asymmetry 11 ( 6 ) 1397 - 1403 2000年04月

Synthesis and Synthetic Application of α-Formylvinylphosphonates. Facile Synthesis of Phosphono-Substituted Heterocyclic Compounds 査読有り

岡内　辰夫

The Journal of Organic Chemistry 65 ( 14 ) 4326 - 4332 2000年04月

Synthesis of 5-Diphenylphosphinolyl-2, 3-dihydropyran-4-ones 査読有り

岡内　辰夫

Heterocycles 53 ( 3 ) 1393 - 1398 2000年04月

General Method for Acylation of Indoles at 3-Position with Acyl Chlorides in the Presence of Dialkylaluminum Chloride 査読有り

岡内　辰夫

Organic Letters 2 ( 10 ) 1485 - 1487 2000年04月

A Focused Compound Library of Novel N-(7-Indolyl)benzenesulfonamides for the Discovery of Potent Cell Cycle Inhibitors 査読有り

岡内　辰夫

Bioorganic & Medicinal Chemistry Letters 10 ( 11 ) 1223 - 1226 2000年04月

The Nucleophilic 5-endo-trig Cyclization of gem-Difluoroolefins with Homoallylic Functional Group : Syntheses of Ring-fluorinated Dihydroheteroaromatics 査読有り

岡内　辰夫

Chemical Communications ( 19 ) 1887 - 1888 2000年04月

Synthesis of 5-diphenylphosphinoyl-2,3-dihydropyran-4-ones 査読有り

Okauchi T., Nagamori H., Kouno R., Ichikawa J., Minami T.

Heterocycles 52 ( 3 ) 1393 - 1398 2000年03月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

5-Diphenylphosphinoyl-2,3-dihydropyran-4-ones are readily prepared from the corresponding 5-diphenylphosphinoyl-1-buten-3-yne under mild acidic conditions. The phosphorus substituted pyrones are converted to more substituted pyrones via 1,4-addition of copper reagents followed by Homer- Wittig reaction.

DOI： 10.3987/COM-99-S131

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Vinylic C-F bond activation with low-valent zirconocene: The generation and cross-coupling reactions of 1-fluorovinylzirconocene 査読有り

Fujiwara M., Ichikawa J., Okauchi T., Minami T.

Tetrahedron Letters 40 ( 40 ) 7261 - 7265 1999年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

(p-2,2-Difluorovinyloxyphenyl)dimethylamine, readily obtained from 2,2,2-trifluoroethanol, is treated with zirconocene equivalent 'Cp2Zr' to generate thermostable 1-fluorovinylzirconocene via a C-F bond cleavage. This 1-fluorovinylzirconocene can be used for C-C bond formation through the cross-coupling with aryl iodides in the presence of palladium catalyst and zinc iodide, leading to (Z)-1-aryl-2-(p-dimethylaminophenoxy)-1-fluoroolefins in good yields.

DOI： 10.1016/S0040-4039(99)01491-4

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α-Phosphonovinyl Nonaflate : Their Synthesis and Cross-Coupling Reactions 査読有り

岡内　辰夫

Tetrahedron Letters 40 ( 29 ) 5337 - 5340 1999年04月

Synthetic Utilization of α-Phosphonovinyl Anions 査読有り

岡内　辰夫

Phosphorus, Sulfur and Silicon 144-146 689 - 692 1999年04月

Discovery of Novel Antitumor Sulfonamides Targeting G1 Phase of the Cell Cycle 査読有り

岡内　辰夫

Journal of Medicinal Chemistry 42 ( 19 ) 3789 - 3799 1999年04月

Vinylic C-F Bond Activation : Generation and Cross-Coupling Reactions of 1-Fluorovinylzirconocene 査読有り

岡内　辰夫

Tetrahedron Letters 40 ( 40 ) 7261 - 7265 1999年04月

A Facile Synthesis of 1-H-2, 2-Difluorovinylphosphorus Compounds from 2, 2, 2-Trifluoroethyl Trifluoromethanesulfonate and Substitutions of Their Vinylic Fluorines 査読有り

岡内　辰夫

Journal of Fluorine Chemistry 97 ( 1-2 ) 109 - 114 1999年04月

Synthetic utilization of α-phosphonovinyl anions 査読有り

Minami T., Kouno R., Okauchi T., Nakamura M., Ichikawa J.

Phosphorus, Sulfur and Silicon and Related Elements 144-146 689 - 692 1999年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

The α-phosphonovinyl anions, generated in situ from treatment of β-hetero-substituted vinylphosphonates 1a-c with LDA (or LTMP), were trapped with various electrophiles such as chlorotriorganosilanes, chlorotrimethylgermane, chlorotriorganotins, dimethyl disulfide, and halogen to afford the corresponding β-hetero-substituted α-functionalized vinylphosphonates 2-14 in good to excellent yields. The Friedel-Crafts reaction of α-(silyl) or α-(germyl)phosphonoketene dithioacetals 2, 9 or 4 with acid chlorides gave α-acylated phosphonoketene dithioacetals 15-19 in 53-91 % yields. The palladium-catalyzed cross-coupling reaction of β-ethoxy-α-(tributylstannyl)vinylphosphonate 13 with a variety of organic halides (R = acyl, allyl, aryl etc.) provided β-ethoxy-α-substituted vinylphosphonates 20-25 in good to moderate yields. The palladium-mediated cross-coupling reaction of α-(iodo)-vinylphosphonates 7, 14 with terminal acetylenes afforded α-alkynylated vinylphosphonates 26-29 in 69-83 % yields.

DOI： 10.1080/10426509908546338

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Synthesis and Synthetic Utilization of α-Functionalized Vinylphosphonates Bearing β-Oxy or β-Thio Substituents 査読有り

Kouno R., Okauchi T., Nakamura M., Ichikawa J., Minami T.

Journal of Organic Chemistry 63 ( 18 ) 6239 - 6246 1998年09月

記述言語：英語掲載種別：研究論文（学術雑誌）

The β-hetero-substituted vinylphosphonates la-c on treatment with LDA or LTMP were readily lithiated at the α-position of the phosphono group, and the resulting α-lithiovinylphosphonates were trapped with various electrophiles to afford the corresponding α-functionalized vinylphosphonates 2-14 in 55-96% yields. The Friedel-Crafts reaction of α-(silyl)- or a-(germyl)-phosphonoketene dithioacetals 2, 9, or 4 with acid chlorides gave α-acylated phosphonoketene dithioacetals 15-19 in 53-91% yields. The palladium-catalyzed cross-coupling reaction of β-ethoxy-α-(tributylstannyl)vinylphosphonate 13 with a variety of organic halides (R = acyl, allyl, aryl, etc.) provided β-ethoxy-α-substituted vinylphosphonates 21-26 in good to moderate yields. The palladium-mediated cross-coupling reaction of α-(iodo)vinylphosphonates 7 and 14 with terminal acetylenes afforded α-alkynylated vinylphosphonates 41-44 in 69-83% yields. Several α-functionalized β-hetero-substituted vinylphosphonates were applied to the synthesis of pyrazoles and an isoxazole possessing a phosphono function.

DOI： 10.1021/jo980467g

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Fluorine-directed Nazarov cyclizations 2: Regioselective synthesis of 5-trifluoromethyl-2-Cyclopentenones 査読有り

Ichikawa J., Fujiwara M., Okauchi T., Minami T.

Synlett ( 8 ) 927 - 929 1998年08月

記述言語：英語掲載種別：研究論文（学術雑誌）

1-Trifluoromethylvinyl vinyl ketones are treated with trimethylsilyl trifluoromethanesulfonate in CH 2 Cl 2 -1,1,1,3,3,3-hexafluoro-2-propanol to afford 5-trifluoromethyl-2-cyclopentenones. Both acyclic and cyclic substrates furnish the corresponding cyclized products in good to excellent yields with defined placement of the endocyclic double bond due to the strong electronic effect exerted by the trifluoromethyl group.

DOI： 10.1055/s-1998-1817

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Fluorine-Directed Nazarov Cyclizations 2 : Regioselective Synthesis of 5-Trifluoromethyl-2-2cyclopentenones 査読有り

岡内　辰夫

Synlett ( 8 ) 927 - 929 1998年04月

Synthesis and Synthetic Utilization of α-Functionalized Vinylphosphonates Bearing β-Oxy or β-Thio Substituents 査読有り

岡内　辰夫

The Journal of Organic Chemistry 63 ( 18 ) 6239 - 6246 1998年04月

Lewis Acid-Catalyzed Intramodecular [2+2]Cydoaddition of α-Ester-Substituted Conjugated Dienyl and Trienylphosphonates. New Synthesis of Functionalized Cydic Terpenoids 査読有り

岡内　辰夫

The Journal of Organic Chemistry 62 ( 24 ) 8419 - 8424 1997年04月

2-Phosphono-1,1,4,4-tetrathio-1,3-butadienes. Synthesis and Synthetic Application to Highly Functionalized Dienes and Heterocycles 査読有り

岡内　辰夫

Bulletin des Soci(]J1117[)t(]J1117[)s Chimique Belges 106 ( 9-10 ) 525 - 532 1997年04月

5-endo-Trigonal Cyclization of o-Substituted gem-Difluorostyrenes : Syntheses of 2-Fluorinated Indoles, Benzo[b]furans, and Benzo[b]thiophenes 査読有り

岡内　辰夫

Chemical Communications ( 16 ) 1537 - 1538 1997年04月

5-endo-Trigonal cyclization of o-substituted gem-difluorostyrenes: Syntheses of 2-fluorinated indoles, benzo[b]furans and benzo[b]thiophenes 査読有り

Ichikawa J., Wada Y., Okauchi T., Minami T.

Chemical Communications ( 16 ) 1537 - 1538 1997年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

β,β-Difluorostyrenes bearing tosylamido, hydroxy or methylsulfinyl groups at the o-position undergo intramolecular substitution of the nitrogen, oxygen or sulfur with loss of fluorine via a 5-endo-trigonal process leading to 2-fluorinated heterocyclic systems in high yields.

DOI： 10.1039/a703110f

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Lewis Acid-Catalyzed Intramolecular [2 + 2] Cycloaddition of α-Ester-Substituted Conjugated Dienyl- And Trienylphosphonates. New Synthesis of Functionalized Cyclic Terpenoids 査読有り

Okauchi T., Kakiuchi T., Kitamura N., Utsunomiya T., Ichikawa J., Minami T.

Journal of Organic Chemistry 62 ( 24 ) 8419 - 8424 1997年01月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

α-Ester-substituted 1,3-dienylphosphonates 7 and 8, prepared by the Knoevenagel condensation, underwent intramolecular [2 + 2] cycloaddition in the presence of Lewis acid to form bicyclo[4.2.0] (26-57% yield) and bicyclo[3.2.0]skeleton (14-38% yield), respectively. Similar treatment of homologous 1,3-dienylphosphonate 11 and 1,3,5-trienylphosphonate 12 resulted in the formation of ionone derivatives (30-94% yield). The intramolecular cycloaddition reaction was applicable to several conjugated dienes bearing an ester group.

DOI： 10.1021/jo971153g

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Synthesis and synthetic application of phosphonoketene dithioacetals. New synthesis of dithioallenes and (α-dithiocarboxyvinyl)phosphonates 査読有り

Minami T., Okauchi T., Matsuki H., Nakamura M., Ichikawa J., Ishida M.

Journal of Organic Chemistry 61 ( 23 ) 8132 - 8140 1996年11月

記述言語：英語掲載種別：研究論文（学術雑誌）

Phosphonoketene dithioacetals 3a-e were obtained in good yields by the reaction of ethyl phosphonoacetates 1a,b with 2-4 equiv of thiols 2a-c in the presence of an alkylaluminum dichloride or dialkylaluminum chlorides. Reaction of 2,2-dithio-1-phosphonovinyl anions with aldehydes afforded allylic alcohols 4-7, 11-18 in good to moderate yields. Treatment of the alcohols 4-6 with t-BuOK in THF led to symmetrical [2 + 2] cycloadducts 20-22 of 1,1-(ethylenedithio)allenes in moderate yields, while a similar reaction of the alcohols 11-13 produced a mixture of symmetrical and unsymmetrical [2 + 2] cycloadducts of 1,1-(trimethylenedithio)allenes, 23a-25a and 23b-25b, in 55-94% yields. The alcohol 15 on a similar treatment gave 3-tert-butyl-1,1-bis(ethylthio)allene (26) in quantitative yield. The structures of 20 and 23b were determined by X-ray analysis. Treatment of the alcohols 15 and 18 with trifluoromethanesulfonic acid/n-Bu4NX (X = Br, I) or triphenylphosphine/CBr4 in CH2Cl2 afforded α-phosphonodithioacryclic acid esters 34 and 35 in 25-52% yields. The tandem Michael-Wittig reaction of 35 with sodium salt of 2-pyrrolecarbaldehyde in DMF gave ethyl 3-phenyl-3H-cyclopenta[a]pyrrole-2-dithiocarboxylate (36) in 25% yield.

DOI： 10.1021/jo960491z

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0029827951&origin=inward

Development of Chiral Phosphine Ligands Bearing a Carboxyl Group and Their Application to Catalytic Asymmetric Reaction 査読有り

岡内　辰夫

Tetrahedron : Asymmetry 6 ( 10 ) 2469 - 2474 1996年04月

synthesis and Synthetic Application of Phosphonoketene Dithioacetals. New Synthesis of Dithioallenes and (α-Dithio carboxyvinyl) phosphonatis. 査読有り

岡内　辰夫

The Journal of Organic Chemistry 23 ( 61 ) 8132 - 8140 1996年04月

Novel 2, 2-Difluorovinylzirconocene : A Facile Synthesis of Monosubstituted gem-Difluoroolefins via Its Cross-Coupling Reaction 査読有り

岡内　辰夫

Tetrahedron Letters 37 ( 48 ) 8799 - 8802 1996年04月

Development of chiral phosphine ligands bearing a carboxyl group and their application to catalytic asymmetric reaction 査読有り

Minami T., Okada Y., Otaguro T., Tawaraya S., Furuichi T., Okauchi T.

Tetrahedron: Asymmetry 6 ( 10 ) 2469 - 2474 1995年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

A new chiral phosphine ligand bearing a carboxyl group, 3-(diphenylphosphino)butanoic acid, was developed and used for palladium catalyzed asymmetric allylic alkylation of cyclic cis-allylic acetates such as 2-cyclopentenyl, 2-cyclohexenyl, and 2-cycloheptenyl acetate. These acetates reacted with triethyl sodiophosphonoacetate in the presence of the palladium catalyst with the ligand to give the corresponding alkylation products in good enantiomeric excesses. © 1995.

DOI： 10.1016/0957-4166(95)00322-G

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0028895231&origin=inward

Novel 6-5 Fused Ring Heterocycle Antifolates with Potent Antitumor Activity : Bridge Modifications and Heterocyclic Benzoyl Isosters of 2, 4-Diamino-6, 7-dihydro-5H-cyclopenta[d]pyrimidine Antifolate 査読有り

岡内　辰夫

Chemical & Pharmaceutical Bulletin 43 ( 5 ) 829 - 841 1995年04月

Novel 6–5 Fused Ring Heterocycle Antifolates with Potent Antitumor Activity: Bridge Modifications and Heterocyclic Benzoyl Isosters of 2,4-Diamino-6,7-dihydro-5H-cyclopenta[d] pyrimidine Antifolate 査読有り

Kotake Y., Okauchi T., Iijima A., Yoshimatsu K., Nomura H.

Chemical and Pharmaceutical Bulletin 43 ( 5 ) 829 - 841 1995年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

Structural modifications of an extremely potent inhibitor of dihydrofolate reductase (DHFR) activity and tumor cell growth, N-[4-[3-(2,4-diamino-6,7-dihydro-5H-cyclopenta[d]pyrimidin-5-yl)propyl]benzoyl]-L-glutamic acid (1), have led to the synthesis of new cyclopenta[d]pyrimidine-based antifolates, including those with low alkyl substituted trimethylene bridges (2a, b) and isosterically modified bridges (ethyleneoxa, 2c; ethyleneamino, 2d; the N-methyl- and N-ethyl derivatives of 2d, 2e, f) and those in which the benzene ring of 1 has been replaced by heterocyclic isosters (indole, 2g; indoline, 2h; thiophene, 2i). These new analogs are highly potent as DHFR and cell growth inhibitors, and most of them are more potent than methotrexate (MTX) and 10-ethyl-10-deazapterin (10-EDAM) in inhibiting tumor cell growth (P388 MTX-sensitive and MTX-resistant, colon 26 and KB) on 72 h drug exposure. Among them, 2a (the 10-methyl derivative of 1) and 2i were most potent, being 2- to 3-fold more potent than 10-EDAM. On 4 h drug exposure, the growth-inhibitory activity of these analogs was radically influenced by even minor structural changes. Compounds 1, 2a—e, g—i were much more cytotoxic in colon 26 cell line than were MTX and 10-EDAM, with 2d and 2i being most potent, followed by 2a. Structure-activity relationships and their possible significance are discussed. © 1995, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.43.829

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0029032398&origin=inward

Oxydative Generation of Thioalkyl Cation from 2-Tributylstannyl-1, 3-ditianes and 1-(Tributylstannnyl)alkyl Sulfides and Their Reactions with Olefinic Nucleophiles 査読有り

岡内　辰夫

Bulletin of the Chemical Society of Japan 66 ( 10 ) 2995 - 3003 1993年04月

Generation of Cation Radicals from 2-Tributylstannyl-1, 3-dithianes and Their Reaction with Olefins 査読有り

岡内　辰夫

Chemistry Letters ( 7 ) 1229 - 1232 1992年04月

Generation of Cation Radicals from Enamines and Their Reactions with Olefins 査読有り

岡内　辰夫

Chemistry Letters ( 10 ) 2099 - 2102 1992年04月

Generation of Cation Radicals from Allylic Sulfides and Their Reactions with Silyl Enol Ethers by the Use of Cerium(IV)Ammonium Nitrate 査読有り

岡内　辰夫

Chemistry Letters ( 3 ) 515 - 518 1991年04月

Addition Reactions of Cation Radicals of Nitroalkanes to Olefinic Compounds by the Use of Manganese((]G0003[))2-Pyridinecarboxylate 査読有り

岡内　辰夫

Chemistry Letters ( 3 ) 423 - 426 1991年04月

Stereoselective β-C-and β-S-Glycosylation of 2-Deoxyribofuranose Derivatives Controlled by the 3-Hydroxy Protecrive Group 査読有り

岡内　辰夫

Bulletin of the Chemical Society of Japan 62 ( 3 ) 845 - 852 1989年04月

The Addition Reaction of β-Keto Carboxylic Acids to Olefinic Compounds by the Use of Mn((]G0003[))Tris(2-pyridinecarboxylate)as an Oxidant 査読有り

岡内　辰夫

Chemistry Letters ( 12 ) 2169 - 2172 1989年04月

Synthesis of β-2-Deoxyribonucleosides from 1-O-Acetyl-3-O-[2-(methylsulfinyl)ethyl]-2-deoxyribose 査読有り

岡内　辰夫

Chemistry Letters ( 5 ) 801 - 804 1989年04月

The Trityl Cation Mediated Michael Reaction of Ethylthioketene Dithioacetals with Silyl Enol Ethers 査読有り

岡内　辰夫

Chemistry Letters ( 9 ) 1691 - 1694 1987年04月

The Trityl Cation Catalyzed Michael Type Reaction of Stannylated Nucleophiles with Ethylthioketene Dithioacetals 査読有り

岡内　辰夫

Chemistry Letters ( 9 ) 1695 - 1698 1987年04月

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