研究者詳細 - 北村　充

論文 - 北村　充

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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：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）

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

Kyutacar

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

Kitamura M., Fukuzumi N., Shinagawa M., Araki K., Shimizu Y., Takahashi S., Iwata T., Shimooka H., Okauchi T.

Tetrahedron Letters 125 2023年07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）

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

Scopus

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

Kitamura M., Eto T., Konai K., Takahashi S., Shimooka H., Okauchi T.

European Journal of Organic Chemistry 2022 ( 18 ) 2022年05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）

The first efficient diazo-transfer reaction of phenols is described. o-Quinone diazides (diazoquinones) were prepared from phenols in high yields by the diazo-transfer reaction using 2-azido-1,3-bis(2,6-diisopropylphenyl)imidazolium hexafluorophosphate (IPrAP, 2-PF6), which is a safe and stable crystalline. The reaction efficiently proceeded in methanol in the presence of a base. Phenols substituted with electron-donating groups reacted more smoothly than those having electron withdrawing groups. Reactive phenols were diazotized by IPrAP with iPr2NH as a base, and low reactive phenols were diazotized with N,N-dimethyl-4-aminopyridine (DMAP). Furthermore, the formed diazoquinones reacted with sodium azide in 2-methoxyethanol and afforded the corresponding azidophenol in high yields.

DOI： 10.1002/ejoc.202200307

Kyutacar

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

Hammill M.L., Tsubaki K., Kitamura M., Okauchi T., Desaulniers J.P.

Current Protocols 3 ( 10 ) 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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Conversion of η4-(Vinylketene)iron complexes to η4-(Vinylketenimine)iron complexes using titanium chloride and amines 査読有り国際誌

Tatsuo Okauchi, Kohei Teratani, Tomoya Nakagawa, Taiga Ichimura, Hirokazu Shimooka, Mitsuru Kitamura

Journal of Organometallic Chemistry ( Elsevier B.V. ) 990 Article number 122672 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）

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 招待有り査読有り国際誌

Desaulniers J.P., Tsubaki K., Hammill M.L., Kitamura M., Okauchi T.

Current Protocols 3 ( 5 ) 2023年05月

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. © 2023 Wiley Periodicals LLC. Basic Protocol 1: Synthesis of a DMT- and TBS-protected unsymmetrical dinucleotide. Basic Protocol 2: Synthesis of a DMT-protected unsymmetrical dinucleotide phosphotriester monoalcohols. Basic Protocol 3: Synthesis of DMT-protected phenylethyl phosphotriester dinucleotide phosphoramidites. Basic Protocol 4: Synthesis, purification, and characterization of RNAs containing triester phosphate modifications.

DOI： 10.1002/cpz1.784

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抗菌ペプチドの新たな機能と応用査読有り

ファラグヒシャム, 下岡弘和, 北村充

産業医大誌 ( 学校法人産業医科大学 ) 45 ( 1 ) 1 - 7 2023年03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）

<p>The emergent disaster of antimicrobial resistance developed by virulent bacteria has highlighted the need to investigate substitutes for the presently existing antibiotics. Antibacterial peptides (ABPs) have arisen as promising substitutes because of their unique killing effect on bacteria: bacterial resistance toward ABPs is negligible. ABPs have many beneficial subsidiary effects, such as protection of labile bioactive compounds, and they can be covalently connected to different materials to enhance their antibacterial effect. Many researchers have investigated many applications of these peptides recently, such as in a variety of pharmaceutical dosage forms and wastewater treatment.</p>

DOI： 10.7888/juoeh.45.1

Scopus

CiNii Research

PubMed

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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 2023年01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）

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

Matthew L.Hammill, Kouta Tsubaki, Yuwei Wang, Golam Islam, Mitsuru Kitamura,Tatsuo Okauchi, Jean-Paul Desaulniers

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

Hammill M.L., Tsubaki K., Salim L., Varley A.J., Giorgees I., Kitamura M., Okauchi T., Desaulniers J.P.

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

Kitamura M., Hiroki S., 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）

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

Scopus

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

Hammill M.L., Salim L., Tsubaki K., Varley A.J., Kitamura M., Okauchi T., Desaulniers J.P.

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

Okauchi T., Urakawa A., Tabuchi N., Arai M., Nakagawa T., Ichimura T., Shimooka H., Kitamura M.

Organometallics 40 ( 17 ) 2929 - 2933 2021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）

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

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New Phosphorylating Agents for the Synthesis of Phosphatidylethanolamines 査読有り

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

Synthesis (Germany) 53 ( 20 ) 3827 - 3835 2021年01月

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

Scopus

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

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：責任著者記述言語：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

Kyutacar

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

Tsubaki K., Hammill M.L., Varley A.J., Kitamura M., Okauchi T., Desaulniers J.P.

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

Scopus

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Improvement of the novel inhibitor for Mycobacterium enoyl-acyl carrier protein reductase (InhA): a structure–activity relationship study of KES4 assisted by in silico structure-based drug screening 査読有り

Taira J., Umei T., Inoue K., Kitamura M., Berenger F., Sacchettini J.C., Sakamoto H., Aoki S.

Journal of Antibiotics 73 ( 6 ) 372 - 381 2020年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020, The Author(s), under exclusive licence to the Japan Antibiotics Research Association. InhA or enoyl-acyl carrier protein reductase of Mycobacterium tuberculosis (mtInhA), which controls mycobacterial cell wall construction, has been targeted in the development of antituberculosis drugs. Previously, our in silico structure-based drug screening study identified a novel class of compounds (designated KES4), which is capable of inhibiting the enzymatic activity of mtInhA, as well as mycobacterial growth. The compounds are composed of four ring structures (A–D), and the MD simulation predicted specific interactions with mtInhA of the D-ring and methylene group between the B-ring and C-ring; however, there is still room for improvement in the A-ring structure. In this study, a structure–activity relationship study of the A-ring was attempted with the assistance of in silico docking simulations. In brief, the virtual chemical library of A-ring-modified KES4 was constructed and subjected to in silico docking simulation against mtInhA using the GOLD program. Among the selected candidates, we achieved synthesis of seven compounds, and the bioactivities (effects on InhA activity and mycobacterial growth and cytotoxicity) of the synthesized molecules were evaluated. Among the compounds tested, two candidates (compounds 3d and 3f) exhibited superior properties as mtInhA-targeted anti-infectives for mycobacteria than the lead compound KES4.

DOI： 10.1038/s41429-020-0293-6

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Structural modification of a novel inhibitor for mycobacterium enoyl-acyl carrier protein reductase assisted by in silico structure-based drug screening 査読有り

Taira J., Nagano T., Kitamura M., Yamaguchi M., Sakamoto H., Aoki S.

International Journal of Mycobacteriology 9 ( 1 ) 12 - 17 2020年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 Medknow. All rights reserved. Background: Mycobacterium tuberculosis enoyl-acyl carrier protein reductase (mtInhA) is involved in the biosynthesis of mycolic acids, a major component of mycobacterial cell walls, and has been targeted in the development of anti-tuberculosis (TB) drugs. In our previous in silico structure-based drug screening study, we identified KES4, a novel class of mtInhA inhibitor. KES4 is composed of four ring structures (A-D-rings) and molecular dynamic simulation predicted that the D-ring is essential for the interaction with mtInhA. Methods: The structure-activity relationship study of the D-ring was attempted and aided by in silico docking simulations to improve the mtInhA inhibitory activity of KES4. A virtual chemical library of the D-ring-modified KES4 was then constructed and subjected to in silico docking simulation against mtInhA using the GOLD program. The candidate compound showing the highest GOLD score, referred to as KEN1, was synthesized, and its biological properties were compared with those of the lead compound KES4. Results: We achieved the synthesis of KEN1 and evaluated its effects on InhA activity, mycobacterial growth, and cytotoxicity. The antimycobacterial activity of KEN1 was comparable to that of the lead compound (KES4), although it exhibited superior activity in mtInhA inhibition. \Conclusions: We obtained a KES4 derivative with high mtInhA inhibitory activity by in silico docking simulation with a chemical library consisting of a series of D-ring-modified KES4.

DOI： 10.4103/ijmy.ijmy_184_19

Scopus

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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

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

Tetrahedron Letters 61 ( 20 ) 2020年01月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 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

Kyutacar

Scopus

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

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

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

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

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Design, Synthesis and Anticancer Evaluation of New Substituted Thiophene-Quinoline Derivatives 査読有り

Othman D., Selim K., El-Sayed M., Tantawy A., Amen Y., Shimizu K., Okauchi T., Kitamura M.

Bioorganic and Medicinal Chemistry 27 ( 19 ) 2019年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2019 Elsevier Ltd A series of new isoxazolyl, triazolyl and phenyl based 3-thiophen-2-yl-quinoline derivatives were synthesized adopting click chemistry approach. In addition, the synthesis of new useful synthon, (2-chloroquinolin-3-yl) (thiophen-2-yl) methanol, is reported. The obtained compounds were characterized by spectral data analysis and evaluated for their anticancer activity. All the derivatives were subjected to in vitro MTT cytotoxicity screening assay against a panel of four different human cancer cell lines, liver (HepG-2), colon (HCT-116), human cervical cancer (HeLa) and breast (MCF-7). Out of a library of 17 compounds, two compounds have been identified as potent and selective cytotoxic agents against HeLa and MCF-7 cell lines. SAR studies for such hybridized analogues were investigated and phenyl derivatives were proved to be more potent than isoxazole and triazole derivatives. Furthermore, the promising compounds were selected for in vitro inhibition of EGFR-TK and Topo II enzymes. Also, they were subjected to cell cycle arrest analysis and apoptosis assay on MCF-7 cells. Our recent finding highlights these thiophene-quinoline analogues as a promising class of compounds for further studies concerning new anticancer therapies.

DOI： 10.1016/j.bmc.2019.07.042

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Direct Azidation of Phenols 査読有り

Kitamura M., Murakami K., Koga T., Eto T., Ishikawa A., Shimooka H., Okauchi T.

European Journal of Organic Chemistry 2019 ( 33 ) 5824 - 5827 2019年09月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Direct azidation of phenols was developed. By treating chloroimidazolinium chloride 1b and sodium azide with phenol in the presence of a secondary amine in methoxyethanol, ortho-azidation of phenol was achieved.

DOI： 10.1002/ejoc.201900967

Kyutacar

Scopus

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高校生のためのクロスカップリング実験査読有り

岡内　辰夫，北村　充

化学と教育 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 ( 公益社団法人日本化学会 ) 48 ( 1 ) 28 - 31 2019年01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 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

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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：最終著者記述言語：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

CiNii Article

CiNii Research

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

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

T. Okauchi, S. Nakamura, K. Tsubaki, M. Asakawa, M. Kitamura

Carbohydrate Research 448 24 - 27 2017年08月

Synthesis of 1,2-naphthalenediol derivatives by Rh-catalyzed intermolecular O-H insertion reaction of 1,2-diazonaphthoquinones with water and alcohol 査読有り

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

Tetrahedron Letters 58 ( 36 ) 3508 - 3511 2017年07月

Azidoimidazolinium Salts: Safe and Efficient Diazo-transfer Reagents and Unique Azido-donors 査読有り

Kitamura M.

Chemical Record 17 ( 7 ) 653 - 666 2017年07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）

© 2017 The Chemical Society of Japan & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2-Azido-1,3-dimethylimidazolinium chloride (ADMC) and its corresponding hexafluorophosphate (ADMP) were found to be efficient diazo-transfer reagents to various organic compounds. ADMC was prepared by the reaction of 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and sodium azide. ADMP was isolated as a crystal having good thermal stability and low explosibility. ADMC and ADMP reacted with 1,3-dicarbonyl compounds under mild basic conditions to give 2-diazo-1,3-dicarbonyl compounds in high yields, which were easily isolated in virtue of the high water solubility of the by-products. ADMP showed high diazo-transfer ability to primary amines even in the absence of metal salt such as Cu(II). Using this diazotization approach, various alkyl/aryl azides were directly obtained from their corresponding primary amines in high yields. Furthermore, naphthols reacted with ADMC to give the corresponding diazonaphthoquinones in good to high yields. In addition, 2-azido-1,3-dimethylimidazolinium salts were employed as azide-transfer and migratory amidation reagents.

DOI： 10.1002/tcr.201600118

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

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

Synlett 29 ( 4 ) 457 - 462 2017年03月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

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

Kyutacar

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Diazonaphthoquinones: Synthesis, reactions and applications 招待有り査読有り

D.I.A. Othman, M. Kitamura,

Heterocycles 92 ( 10 ) 1761 - 1783 2016年08月

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

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

J. Org. Chem. 2016年04月

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

M. Kitamura, A. Ishikawa, T. Okauchi

Tetrahedron Lett. 57 ( 16 ) 1794 - 1797 2016年03月

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

M. Kitamura, S. Takahashi, T. Okauchi

J. Org. Chem. 80 ( 16 ) 8406 - 8416 2015年08月

Synthesis of 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate 査読有り

M. Kitamura, K. Murakami

Organic Syntheses 92 171 - 181 2015年05月

Synthesis of the Cyclic Prenylguanidine Nitensidine E using a Palladium-Catalyzed Carbenylative Amination 査読有り

M. Kitamura, R. Yuasa, D. L. Van Vranken

Tetrahedron Lett. 2014年11月

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

Kitamura M., Kato S., Yano M., Tashiro N., Shiratake Y., Sando M., Okauchi T.

Organic and Biomolecular Chemistry 12 ( 25 ) 4397 - 4406 2014年07月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

Organic azides were prepared from primary amines in high yields by a metal free diazo-transfer reaction using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N,N-dimethyl)aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses. © the Partner Organisations 2014.

DOI： 10.1039/c4ob00515e

Scopus

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

M. Kitamura, S. Kato, M. Yano, N. Tashiro, Y. Shiratake, M. Sando, T. Okauchi

Org. Biomol. Chem. in press 2014年05月

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

M. Kitamura, M. Kisanuki, K. Kanemura, T. Okauchi

Org. Lett. 16 1554 - 1557 2014年04月

Development of safe diazo-transfer reagent: Synthesis and reaction of guanidino diazoninm salt (azide imidazolinium salt) 査読有り

Kitamura M.

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 72 ( 1 ) 14 - 25 2014年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

2-Azido-l,3-dimethylimidazolinium chloride (ADMC) and its corresponding hexafluorophosphate (ADMP) were found to be safe and efficient diazo-transfer reagents to various organic compounds. ADMC was prepared by the reaction of 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and sodium azide. ADMP was isolated as a crystal having thermal stability and low explo- sibility. ADMC and ADMP reacted with 1,3-dicarbonyl compounds under mild basic conditions to give 2-diazo-1,3-dicarbonyl compounds in high yields, which are easily isolated because the byproducts are highly soluble in water. Naphthols also reacted with ADMC to give corresponding diazonaphthoquinones in good to high yields. Furthermore, ADMP shows efficient diazo-transfer ability to primary amines even without the aid of a metal salt such as Cu(ll). Using this diazoti- zation approach, various alkyl/aryl azides were obtained directly from corresponding primary amines in high yields. In addition, ADMC/ADMP could be used as azide-transfer and amidation reagents.

DOI： 10.5059/yukigoseikyokaishi.72.14

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Synthetic study of kosinostatin aglycone: Synthesis of BCDE rings using alkoxycarbonylmethylation of diazonaphthoquinone 査読有り

M. Kitamura, K. Kubo, S. Yoshinaga, H. Matsuzaki, K. Ezaki, T. Matsuura, D. Matsuura, N. Fukuzumi, K. Araki, M. Narasaki

Tetrahedron Lett. 55 1653 - 1656 2014年01月

Synthesis of α-Arylcarboxylic acid amides from silyl enol ether via migratory Amidation with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate 査読有り

Kitamura M., Murakami K., Shiratake Y., Okauchi T.

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

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

α-Arylcarboxylic acid amides were synthesized by reacting silyl enol ethers of aryl ketones and 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP,1). Silyl enol ethers react with ADMP 1 to give N-(α-arylacyl) guanidines via the migration of aryl groups in enol ethers. The products were transformed to the corresponding α-aryl acetamides by treating with LiAlH4. © 2013 The Chemical Society of Japan.

DOI： 10.1246/cl.130195

Scopus

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

M. Kitamura, K. Araki, H. Matsuzaki, T. Okauchi

Eur. J. Org. Chem. 5045 - 5049 2013年06月

Identification of Compounds with Potential Antibacterial Activity against Mycobacterium through Structure-Based Drug Screening 査読有り

T. Kinjo, Y. Koseki, M. Kobayashi, A. Yamada, K. Morita, K. Yamaguchi, R. Tsurusawa, G. Gulten, H. Komatsu, H. Sakamoto, J. C. Sacchettini, M. Kitamura, S. Aoki

J. Chem. Inf. Model. 53 1200 - 1212 2013年04月

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

M. Kitamura, K. Murakami, Y. Shiratake, T. Okauchi

Chem. Lett. 42 691 - 693 2013年04月

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

M. Kitamura, Y. Tokuda, N. Tashiro, T. Okauchi,

Aust. J. Chem. 65 1687 - 1690 2012年10月

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

M. Kitamura, T. Koga, M. Yano, T. Okauchi

Synlett 1335 - 1338 2012年05月

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

M. Kitamura, M. Kisanuki, T. Okauchi

Eur. J. Org. Chem. 905 - 907 2012年04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

担当区分：責任著者記述言語：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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Synthesis of Isoindole Derivatives by Palladium-Catalyzed Domino Reaction of (2-Alkynyl)phenylketone O-Pentafluorobenzoyloximes 査読有り

M. Kitamura, Y. Moriyasu,T. Okauchi

Synlett 643 - 646 2011年04月

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

M. Kitamura, N. Tashiro, S. Miyagawa, T. Okauchi

Synthesis 2011年04月

Palladium-Catalyzed Cross-Coupling Reactions of 2-Diazonaphthoquinones with Arylboronic Acids 査読有り

M. Kitamura, R. Sakata, T. Okauchi

Tetrahedron Lett. 52 1931 - 1933 2011年04月

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

M. Kitamura, M. Kisanuki, R. Sakata, T. Okauchi

Chem. Lett. 40 1129 - 1131 2011年04月

1-Diazonaphthalen-2(1H)-one 査読有り

M. Kitamura, R. Sakata, T. Matsumoto

Acta Cryst. E67 o1951 2011年04月

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

M. Kitamura, S. Miyagawa, T. Okauchi

Tetrahedron Lett. 52 3158 - 3161 2011年04月

Direct synthesis of organic azides from primary amines with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate 査読有り

Kitamura M., Yano M., Tashiro N., Miyagawa S., Sando M., Okauchi T.

European Journal of Organic Chemistry ( 3 ) 458 - 462 2011年01月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

Organic azides were prepared from primary amines in high yields by metal-free diazo transfer with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate, which is a stable, crystalline solid that is easy to handle. Organic azides were prepared from primary amines in high yields by metal-free diazo transfer with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is a stable, crystalline solid that is easy to handle. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/ejoc.201001509

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

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

Synlett 4890 - 4893 2010年04月

Pinacol Coupling of 2,2'-Biaryldiketone: An Application for the Synthesis of Enantiopure 3,4-Dihydrodibenzo[c,g]phenanthrene-3,4-diol Derivatives 査読有り

M. Kitamura, K. Shiomi,K. D. Kitahara, Y. Yamamoto, T. Okauchi

Synlett 1359 - 1362 2010年04月

Direct Synthesis of Acyl Azides from Carboxylic Acids Using 2-Azido-1,3-Dimethylimidazolinium Chloride 査読有り

M. Kitamura, N. Tashiro, Y. Takamoto, T. Okauchi

Chem. Lett. 732 - 733 2010年04月

Enantioselective synthesis of alpha-benzylalanine using trans-3,4-dihydro-3,4-diaryldibenzo[c,g]phenanthrene-3,4-diol 査読有り

M. Kitamura, D. Kitahara, T. Okauchi

Synlett 2097 - 2100 2010年04月

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

M. Kitamura, Y. Shintaku, D. Kudo, T. Okauchi

Tetrahedron Lett. 51 4890 - 4893 2010年04月

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

M. Kitamura, T. Tashiro, T. Okauchi

Synlett 2943 - 2944 2009年04月

Catalytic Radicalcyclization of Oximes 査読有り

M. Kitamura,K.Narasaka

Bull. Chem. Soc. Jpn 81 539 - 547 2008年04月

Synthesis of (-)-sordarin 査読有り

Chiba S,Kitamura M,Narasaka K

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 128 ( 21 ) 6931 - 6937 2007年04月

"General synthesis route to benanomicin-pradimicin antibiotics" 査読有り

Tamiya,M; Ohmori,K; Kitamura,M; Kato,H; Arai,T; Oorui,M ; Suzuki,K.

Chem. Eur. J. 13 9791 - 9823 2007年04月

Synthesis of Primary Amines by the Electrophilic Amination of Grignard Reagents with 1,3-Dioxolan-2-one O-Sulfonyloxime 査読有り

Kitamura,M.; Suga,T.; Chiba,S.; Narasaka,K.

Org. Lett. 6 4619 - 4621 2007年04月

Synthesis of dihydropyrrole derivatives by copper-catalyzed cyclization of gamma,delta-unsaturated ketone O- methoxy￢carbonyloximes 査読有り

Koganemaru,Y.; Kitamura,M.; Narasaka,K.

Chem. Lett. 784 - 785 2007年04月

(-)-ソルダリンの全合成査読有り

北村　充，千葉俊介，奈良坂紘一

有機合成化学協会誌 65 450 - 459 2007年04月

Synthesis of 5-phenyl 2-functionalized pyrroles by amino Heck and tandem amino Heck carbonylation reactions 査読有り

Zaman,S.; Kitamura,M.; Abell,A. D.

Aust. J. Chem. 624 - 626 2007年04月

Synthesis of peduncularine 査読有り

Kitamura M,Ihara Y,Uera K,Narasaka,K

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 79 ( 10 ) 1552 - 1560 2006年04月

Palladium(0)-catalyzed synthesis of pyridines from β-acetoxy-γ,δ-unsaturated ketone oximes 査読有り

Kitamura,M.; Kudo,D.; Narasaka,K.

Arkivoc III 148 - 162 2006年04月

Synthesis of azaheterocycles by one electron reduction of oximes 査読有り

Narasaka,K.; Kitamura,M.

ARKIVOC 7 245 - 260 2006年04月

Synthesis of Trisubstituted Imidazoles by Palladium-Catalyzed Cyclization of O-Pentafluorobenzoylamidoximes: Application to Amino Acid Mimetics with a C-Terminal Imidazole 査読有り

Zaman,S.; Kitamura,M.; Abell,A. D.

Org. Lett. 2005 7 609 - 611 2005年04月

Synthesis of α-Carbolines by Copper-Catalyzed Radical Cyclization of β-3-Indolyl Ketone O-Pentafluorobenzoyloximes 査読有り

Tanaka,K.; Kitamura,M.; Narasaka,K.

Bull. Chem. Soc. Jpn. 78 1659 - 1664 2005年04月

Photochemical Radical Cyclization of γ,δ-Unsaturated Ketone Oximes to 3,4-Dihydro-2H-pyrroles 査読有り

Kitamura,M.; Mori,Y.; Narasaka,K.

Tetrahedron Lett. 46 2373 - 2376 2005年04月

Palladium(0)-Catalyzed Amino-Heck Reaction of γ,δ-Uusaturated Ketone N,N,N-Trimethylhydrazonium Salts 査読有り

Kitamura,M.; Yanagisawa,H.; Yamane,M.; Narasaka,K.

Heterocycles 65 273 - 277 2005年04月

Regio- and Stereocontrolled Total Synthesis of Benanomicin B 査読有り

Ohmori,K.; Tamiya,M.; Kitamura,M.; Kato,H.; Oorui,M.; Suzuki,K.

Angew. Chem., Int. Ed. 44 3871 - 3874 2005年04月

Amination with Oximes 査読有り

Narasaka,K.; Kitamura,M.

Eur. J. Org. Chem. 4505 - 4505 2005年04月

Transformation of 1,5- and 1,6-Dienes by Hydrozirconation and Oxidation with Cerium(IV) Compounds 査読有り

Azemi,T.; Kitamura,M.; Narasaka,K.

Tetrahedron 60 1339 - 1344 2004年04月

Synthesis of 1-Azaazulenes from Cycloheptatrienylmethyl Ketone O-Pentafluorobenzoyloximes by Palladium-Catalyzed Cyclization 査読有り

Chiba,S.; Kitamura,M.; Saku,O.; Narasaka,K.

Bull. Chem. Soc. Jpn. 77 785 - 796 2004年04月

Synthesis of (±)-Sordaricin 査読有り

Kitamura,M.; Chiba,S.; Narasaka,K.

Chem. Lett. 33 942 - 943 2004年04月

「オキシム誘導体を用いる合成反応の新展開」査読有り

北村充,奈良坂紘一

有機合成化学協会誌 62 38 - 48 2004年04月

Synthesis of Primary Amines and N-Methylamines by the Electrophilic Amination of Grignard Reagents with 2-Imidazolidinone O-Sulfonyloxime 査読有り

Kitamura,M.; Chiba,S; Narasaka,K.

Bull. Chem. Soc. Jpn. 76 1063 - 1070 2003年04月

Synthesis of Dihydropyrrole and Pyrrole Derivatives by Radical Cyclization of γ,δ-Unsaturated Ketone O-Acetyloximes 査読有り

Yoshida,M; Kitamura,M.; Narasaka,K.

Bull. Chem. Soc. Jpn. 76 2003 - 2008 2003年04月

Synthesis of Polycyclic Imines by Palladium-Catalyzed Domino Cyclization of Di- and Trienyl Ketone O-Pentafluorobenzoyloximes 査読有り

Zaman,S.; Kitamura,M.; Narasaka,K.

Bull. Chem. Soc. Jpn. 76 1055 - 1062 2003年04月

Synthesis of Quinolines and 2H-Dihydropyrroles by Nucleophilic Substitution at the Nitrogen Atom of Oxime Derivatives 査読有り

Kitamura,M.; Yoshida,M.; Kikuchi,T.; Narasaka,K.

Synthesis 15 2415 - 2426 2003年04月

Intramolecular Substitution Reaction of Lithium Alkylidene Carbenoids: Regioselective Synthesis of Indenes 査読有り

Yanagisawa,H.; Miura,K.; Kitamura,M.; Narasaka,K.; Ando K.

Bull. Chem. Soc. Jpn. 76 2009 - 2026 2003年04月

Amination of Arenes with N,N-Dimethyl-2-imidazolidinone O-Methoxyacetyloxime 査読有り

Baldovini,N.; Kitamura,M.; Narasaka,K.

Chem. Lett. 548 - 549 2003年04月

Synthesis of 3,4-dihydro-2H-pyrroles from gamma,delta-unsaturated ketone O-acetyloximes 査読有り

Yoshida,M.; Kitamura,M.; Narasaka,K

Chem. Lett. 144 - 145 2002年04月

Semi pinacol strategy for constructing B-ring of pradimicin-benanomicin antibiotics 査読有り

Ohmori,K.; Kitamura,M.; Ishikawa,Y.; Kato,H.; Oorui,M.; Suzuki,K.

Tetrahedron lett. 7023 - 7026 2002年04月

Intramolecular substitution reaction of alkylidene-lithium carbenoids: Regioselective synthesis of indenes 査読有り

Yanagisawa,H.; Miura,K.; Kitamura,M.; Narasaka,K.; Ando,K.

Helv. Chim. Acta 85 3130 - 3135 2002年04月

"Synthesis of Aza-Heterocycles from Oximes by Amino-Heck Reaction" 査読有り

Kitamura,M.; Narasaka,K.

Chem. Rec. 2002, 2, 268-277. 2 268 - 277 2002年04月

Palladium-catalyzed synthesis of 1-azaazulenes from cycloheptatrienylmethyl ketone O-pentafluorobenzoyl oximes 査読有り

Kitamura,M.; Chiba,S.; Saku,O.; Narasaka,K.

Chem. Lett. 606 - 607 2002年04月

Synthesis of pyrrole derivatives by palladium-catalyzed cyclization of gamma delta-unsaturated ketone O-pentafluorobenzoyloximes 査読有り

Tsutsui,H.; Kitamura,M.; Narasaka,K.

Bull. Chem. Soc. Jpn. 75 1451 - 1460 2002年04月

Synthesis of spiro imines from oximes by palladinm-catalyzed cascade reaction 査読有り

Kitamura,M.; Zaman,S.; Narasaka,K.

Synlett 974 - 976 2001年04月

Divergent Behavior of Cobalt-Complexed Enyne Having a Leaving Group 査読有り

Kitamura,M.; Ohmori,K.; Suzuki,K.

Tetrahedron Lett. 40 4563 - 4566 1999年04月

From Axial Chirality to Central Chiralities: Pinacol Cyclization of 2,2'-Biaryldicarbaldehyde to trans-9,10-Dihydrophenanthrene-9,10-diol 査読有り

Ohmori,K.; Kitamura,M.; Suzuki,K.

Angew. Chem. Int. Ed. 38 1226 - 1229 1999年04月

Total Synthesis of Pradimicinone, the Common Aglycon of the PradimicinBenanomicin Antibiotics 査読有り

Kitamura,M.; Ohmori,K.; Kawase,T.; Suzuki,K.

Angew. Chem. Int. Ed. 38 1229 - 1232 1999年04月

Theoretical and Experimental Study on the In-Plane SN2 Type Substitution Reaction of Haloalkenes with Inversion of Configuration at Vinylic Carbon 査読有り

Ando,K.; Kitamura,M.; Miura,K.; Narasaka,K.

Org. Lett. 6 2461 - 2463 1996年04月

Nobel Migrating Group in 1,2-Anionotropic Reactions: Cobalt Complexation Facilitates 1,2-Shift of Alkynyl Groups 査読有り

Nagasawa,T.; Taya,K.; Kitamura,M.; Suzuki,K.

J. Am. Chem. Soc. 118 8949 - 8950 1996年04月

Cobalt-Complexation Makes 2-(1-alkynyl)propenes Good Ene Donors in Carbonyl-Ene Reaction 査読有り

Nagasawa,T.; Kitamura,M.; Suzuki,K.

Synlett 1183 - 1186 1995年04月

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