2022/07/25 更新

写真a

ヨシミツ タケヒコ
好光 健彦
YOSHIMITSU Takehiko
所属
医歯薬学域 教授
職名
教授
外部リンク

学位

  • 博士(薬学) ( 東北大学 )

研究キーワード

  • Synthetic organic chemistry

  • Natural product synthesis

  • medicinal chemistry

  • 有機合成化学

  • 天然物合成

  • 医薬化学

研究分野

  • ライフサイエンス / 薬系化学、創薬科学

  • ライフサイエンス / 薬系化学、創薬科学

学歴

  • 東北大学   Graduate School of Pharmaceutical Sciences  

    1992年4月 - 1995年3月

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    国名: 日本国

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  • 東北大学   Graduate School, Division of Pharmaceutical Sciences  

    - 1995年

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  • 東北大学   Graduate School of Pharmaceutical Sciences  

    1990年4月 - 1992年3月

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  • 東北大学   Faculty of Pharmaceutical Sciences  

    1986年4月 - 1990年3月

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    国名: 日本国

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  • 東北大学   Faculty of Pharmaceutical Science  

    - 1990年

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経歴

  • 大阪大学

    2016年 - 2018年

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  • - 岡山大学医歯薬学総合研究科 教授

    2016年

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  • - Professor,Graduate School of Medicine, Dentistry and Pharmaceutical Sciences,Okayama University

    2016年

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  • 徳島大学   Faculty of Engineering, Department of Chemical Science and Technology

    2013年

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  • 九州大学   Institute for Materials Chemistry and Engineering

    2012年

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  • 大阪大学

    2006年 - 2016年

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  • Associate Professor,Graduate School of Pharmaceutical Sciences

    2006年 - 2016年

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  • 明治薬科大学

    2003年 - 2006年

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  • Senior Assistant Professor

    2003年 - 2006年

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  • 明治薬科大学

    1997年 - 2003年

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  • Research Associate

    1997年 - 2003年

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  • マサチューセッツ工科大学(MIT)化学科 博士研究員

    1995年 - 1997年

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委員歴

  • 日本薬学会   日本薬学会代議員  

    2013年4月 - 2016年3月   

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    団体区分:学協会

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  • 公益社団法人有機合成化学協会   有機合成化学協会誌編集協力委員  

    2011年4月 - 2013年3月   

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    団体区分:学協会

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  • The 5th Seoul-Kyoto-Osaka Joint Symposium on Pharmaceutical Sciences for Young Scientists   Organizing committee member  

    2010年5月   

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    団体区分:学協会

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  • 第7回次世代を担う有機化学シンポジウム   実行委員長  

    2009年7月   

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    団体区分:学協会

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  • 第3回日本薬学会化学系薬学部会若手教員会議   議長  

    2009年7月   

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    団体区分:学協会

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  • 公益社団法人日本薬学会   ファルマシアトピックス専門小委員  

    2009年4月 - 2011年3月   

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    団体区分:学協会

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  • 第6回次世代を担う有機化学シンポジウム   世話人  

    2008年5月   

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    団体区分:学協会

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  • 第128会日本薬学会一般シンポジウム「分子の新機能が拓く有機合成化学」   オーガナイザー  

    2008年3月   

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    団体区分:学協会

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  • 第5回次世代を担う有機化学シンポジウム   世話人  

    2007年5月   

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    団体区分:学協会

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  • 日本薬学会   日本薬学会近畿支部委員  

    2007年4月 - 2017年3月   

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    団体区分:学協会

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  • The 3rd Seoul-Kyoto-Osaka Joint Symposium on Pharmaceutical Sciences for Young Scientists   Scientific Committee Member  

    2006年11月   

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    団体区分:学協会

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論文

書籍等出版物

  • クロロスルホリピッド-全合成の新たな標的-

    化学工業  2014年 

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  • Stereoselective Synthesis of Halogenated Natural Products, Chapter 43

    John Wiley & Sons  2013年 

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  • Triethylborane in Handbook of Reagents for Organic Synthesis; Reagents for Direct Functionalization of C-H Bonds

    Wiley-VCH  2006年 

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  • Triethylborane in Encyclopedia of Reagents for Organic Synthesis

    John Wiley & Sons  2005年 

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  • Radical Alpha-Functionalization of Ethers in Handbook of C-H Transformations

    Wiley VCH Verlag GmbH  2005年 

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MISC

  • A Virtual Screening Platform Identifies Chloroethylagelastatin A as a Potential Ribosomal Inhibitor 査読 国際共著

    T. R. Caulfield, K. E. Hayes, Y. Qiu, M. Coban, J. Seok Oh, A. L. Lane, T. Yoshimitsu, L. Hazlehurst, J. A. Copland, H. W. Tun

    10   1047   2020年10月

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    記述言語:英語   掲載種別:速報,短報,研究ノート等(学術雑誌)  

    DOI: 10.3390/biom10101407

    DOI: 10.3390/biom10101407

  • A Virtual Screening Platform Identifies Chloroethylagelastatin A as a Potential Ribosomal Inhibitor 査読

    Thomas R. Caulfield, Karen E. Hayes, Yushi Qiu, Mathew Coban, Joon Seok Oh, Amy L. Lane, Takehiko Yoshimitsu, Lori Hazlehurst, John A. Copland, Han W. Tun

    Biomolecules   10 ( 10 )   1407 - 1407   2020年10月

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    記述言語:英語   掲載種別:速報,短報,研究ノート等(学術雑誌)   出版者・発行元:MDPI AG  

    Chloroethylagelastatin A (CEAA) is an analogue of agelastatin A (AA), a natural alkaloid derived from a marine sponge. It is under development for therapeutic use against brain tumors as it has excellent central nervous system (CNS) penetration and pre-clinical therapeutic activity against brain tumors. Recently, AA was shown to inhibit protein synthesis by binding to the ribosomal A-site. In this study, we developed a novel virtual screening platform to perform a comprehensive screening of various AA analogues showing that AA analogues with proven therapeutic activity including CEAA have significant ribosomal binding capacity whereas therapeutically inactive analogues show poor ribosomal binding and revealing structural fingerprint features essential for drug-ribosome interactions. In particular, CEAA was found to have greater ribosomal binding capacity than AA. Biological tests showed that CEAA binds the ribosome and contributes to protein synthesis inhibition. Our findings suggest that CEAA may possess ribosomal inhibitor activity and that our virtual screening platform may be a useful tool in discovery and development of novel ribosomal inhibitors.

    DOI: 10.3390/biom10101407

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  • Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation 査読

    Eriko Tao, Masaki Inoue, Taejoo Jeong, In Su Kim, Takehiko Yoshimitsu

    The Journal of Organic Chemistry   85 ( 14 )   9064 - 9070   2020年7月

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    担当区分:最終著者, 責任著者   記述言語:英語   掲載種別:速報,短報,研究ノート等(学術雑誌)   出版者・発行元:American Chemical Society (ACS)  

    DOI: 10.1021/acs.joc.0c00965

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  • Chemical Syntheses and Biological Studies of Agelastatin A, a Bioactive Marine Heterocycle Gifted from Nature 招待 査読

    Takehiko Yoshimitsu

    HETEROCYCLES   100 ( 11 )   1735 - 1735   2020年5月

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    担当区分:筆頭著者, 責任著者   記述言語:英語   掲載種別:記事・総説・解説・論説等(学術雑誌)   出版者・発行元:The Japan Institute of Heterocyclic Chemistry  

    DOI: 10.3987/rev-20-929

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  • 天然物合成における窒素フリーラジカル種の戦略的活用:アゲラスタチンAの全合成 査読

    好光 健彦

    有機合成化学協会誌   77 ( 5 )   472 - 481   2019年5月

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    記述言語:日本語   掲載種別:記事・総説・解説・論説等(学術雑誌)  

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  • Ru(II)-Catalyzed C–H Aminocarbonylation of N-(Hetero)aryl-7-azaindoles with Isocyanates

    Jeong, T, Lee, S.-H, Chun, R, Han, S, Han, S.-H, Jeon, Y.-U, Park, J, Yoshimitsu, T, Mishra, N. K, Kim, I.-S

    J. Org. Chem.   83 ( 8 )   4641 - 4649   2018年4月

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  • Visceral Adipose Tissue Drives Cardiac Aging Through Modulation of Fibroblast Senescence by Osteopontin Production

    Sawaki, D, Czibik, G, Pini, M, Ternacle, J, Suffee, N, Mercedes, R, Marcelin, G, Surenaud, M, Marcos, E, Gual, P, Clement, K, Hue, S, Adnot, S, Hatem, S. N, Tsuchimochi, I, Yoshimitsu, T, Henegar, C, Derumeaux, G

    Circulation   2018年

  • Total Synthesis of (-)-Agelastatin A: An SH2’ Radical Azidation Strategy

    Tsuchimochi, I, Kitamura, Y, Aoyama, H, Akai, S, Nakai, K, Yoshimitsu, T

    Chemical Communications   2018年

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  • 2-aminoethoxydiphenyl borate provides an anti-oxidative effect and mediates cardioprotection during ischemia reperfusion in mice

    Hirofumi Morihara, Masanori Obana, Shota Tanaka, Ikki Kawakatsu, Daisuke Tsuchiyama, Shota Mori, Hiroshi Suizu, Akiko Ishida, Rumi Kimura, Izuru Tsuchimochi, Makiko Maeda, Takehiko Yoshimitsu, Yasushi Fujio, Hiroyuki Nakayama

    PLoS ONE   12 ( 12 )   650 - 659   2017年12月

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    記述言語:英語   出版者・発行元:Public Library of Science  

    Excessive levels of reactive oxygen species (ROS) and impaired Ca2+ homeostasis play central roles in the development of multiple cardiac pathologies, including cell death during ischemia-reperfusion (I/R) injury. In several organs, treatment with 2-aminoethoxydiphenyl borate (2-APB) was shown to have protective effects, generally believed to be due to Ca2+ channel inhibition. However, the mechanism of 2-APB-induced cardioprotection has not been fully investigated. Herein we investigated the protective effects of 2-APB treatment against cardiac pathogenesis and deciphered the underlying mechanisms. In neonatal rat cardiomyocytes, treatment with 2-APB was shown to prevent hydrogen peroxide (H2O2) -induced cell death by inhibiting the increase in intracellular Ca2+ levels. However, no 2-APB-sensitive channel blocker inhibited H2O2-induced cell death and a direct reaction between 2-APB and H2O2 was detected by 1H-NMR, suggesting that 2-APB chemically scavenges extracellular ROS and provides cytoprotection. In a mouse I/R model, treatment with 2-APB led to a considerable reduction in the infarct size after I/R, which was accompanied by the reduction in ROS levels and neutrophil infiltration, indicating that the anti-oxidative properties of 2-APB plays an important role in the prevention of I/R injury in vivo as well. Taken together, present results indicate that 2-APB treatment induces cardioprotection and prevents ROS-induced cardiomyocyte death, at least partially, by the direct scavenging of extracellular ROS. Therefore, administration of 2-APB may represent a promising therapeutic strategy for the treatment of ROS-related cardiac pathology including I/R injury.

    DOI: 10.1371/journal.pone.0189948

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  • Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions

    Keita Takubo, Ahmed A. B. Mohamed, Takafumi Ide, Kazuyuki Saito, Takashi Ikawa, Takehiko Yoshimitsu, Shuji Akai

    JOURNAL OF ORGANIC CHEMISTRY   82 ( 24 )   13141 - 13151   2017年12月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    The dienone-phenol rearrangement is a useful tool for the synthesis of highly substituted phenols. In our previous study of the rearrangement of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienone under deoxyfluorination conditions, bond migration proceeded with very poor regioselectivity. In this paper, an acid-mediated rearrangement, of O-perfluoroalkylsulfonyl difluorides with regioselective migration toward the beta'-carbon is reported. This method allowed the synthesis of a fluorinated analog of allocolchicinoids with improved total yield. Successful application to other substrates was also demonstrated.

    DOI: 10.1021/acs.joc.7b02208

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  • Compounds, compositions, and methods of agelastatin alkaloids: patent evaluation of WO2015042239 (A1)

    Takehiko Yoshimitsu, Han W. Tun

    EXPERT OPINION ON THERAPEUTIC PATENTS   27 ( 2 )   113 - 119   2017年2月

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    記述言語:英語   出版者・発行元:TAYLOR & FRANCIS LTD  

    Agelastatins are a family of tetracyclic alkaloids isolated from marine sponges. The patent examined in this publication covers the chemical synthesis of agelastatins A to F and eight analogues and their therapeutic use against hematologic malignancies. The claim on the chemical synthesis features a novel biomimetic cyclization of a tricyclic precursor, which streamlines scalable access to agelastatins and their analogues. This new synthetic approach can potentially expedite the research on these compounds for therapeutic use against cancers by making them more easily available. The claim on the therapeutic use against hematologic malignancies is based on the in vitro cytotoxicity against a limited number of cell lines and can be further strengthened by in vivo therapeutic evaluations focusing on specific hematologic malignancies. The comparative evaluation of the cytotoxicities of the natural alkaloids described in the application greatly enhances the understanding of their structure-activity relationships (SARs) relevant to the development of novel medicinal leads. Overall, the patent application is strong and has the potential to advance the rapidly expanding agelastatin research.

    DOI: 10.1080/13543776.2017.1273902

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  • Radical Cyclization Strategies in Total Syntheses of Bioactive Fused Cyclic Natural Products

    Takehiko Yoshimitsu

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   74 ( 4 )   350 - 359   2016年4月

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    記述言語:日本語   掲載種別:書評論文,書評,文献紹介等   出版者・発行元:SOC SYNTHETIC ORGANIC CHEM JPN  

    The present article discusses our recent endeavors on natural product syntheses wherein radical reactions are strategically employed to access fused carbocycles. Particular emphasis is placed on the radical cyclizations that made it possible to establish the unique bond connectivity and functionalities of the target natural products. The radical chemistry-based approaches to platencin and clavilactone B are discussed here to show the utility of titanocene (III)-mediated epoxy enone cyclization, decarboxylative radical cyclization of an alkynyl carboxylic acid derivative with lead (IV) in 1,4-dioxane, and samarium (II)-mediated radical cyclization-fragmentation of an unsaturated keto ester, all of which serve as versatile means to elaborate the natural products.

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  • Diversity Oriented Synthesis of Allocolchicinoids with Fluoro and/or Oxygen Substituent(s) on the C-Ring from a Single Common Intermediate

    Keita Takubo, Kazunori Furutsu, Takafumi Ide, Hiroyuki Nemoto, Yuko Ueda, Kazutake Tsujikawa, Takashi Ikawa, Takehiko Yoshimitsu, Shuji Akai

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2016 ( 8 )   1562 - 1576   2016年3月

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    記述言語:英語   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Allocolchicinoids, with a distinct polyoxygenated dibenzocycloheptane skeleton, attract much attention as potential candidate anticancer drugs. In this study, eight C-ring fluorinated analogues of allocolchicinoids, seven C-ring oxygen-substituted analogues, and known compounds N-acetylcolchinol and NSC 51046 were synthesized as racemates from a single common intermediate by using either the deoxyfluorination/migration domino reaction or acid-promoted migration as the key step. Among the products obtained, some of the fluorinated derivatives strongly inhibited the growth of prostate DU145 and pancreas Panc 1 cancer cell lines with efficacy comparable to or better than those of N-acetylcolchinol and NSC 51046. They were also less toxic against a non-cancerous cell line than the known compounds were.

    DOI: 10.1002/ejoc.201501624

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  • 生物活性縮環天然物の全合成におけるラジカル環化戦略

    好光健彦

    有機合成化学協会誌   74   350 - 359   2016年

  • 解説「Grob型環開裂」

    有機合成化学協会誌   74   379 - 379   2016年

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  • Total Synthesis of Clavilactone B: A Radical Cyclization− Fragmentation Strategy

    H. Suizu, D. Shigeoka, H. Aoyama, T. Yoshimitsu

    Org. Lett.   17 ( 1 )   126 - 129   2015年1月

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  • A commentary on‘Classic Addition Reaction Gets A Makeover’ in Science & Technology, News of The Week in Chemical & Engineering News

    Takehiko Yoshimitsu

    Chemical & Engineering News   93 ( 3 )   2015年

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  • Enantiospecific Synthesis and Cytotoxicity Evaluation of Ligudentatol: A Programmed Aromatization Approach to the 2,3,4-Trisubstituted Phenolic Motif via Visible-Light-Mediated Group Transfer Radical Cyclization

    Gamal A. I. Moustafa, Hiroshi Suizu, Hiroshi Aoyama, Masayoshi Arai, Shuji Akai, Takehiko Yoshimitsu

    CHEMISTRY-AN ASIAN JOURNAL   9 ( 6 )   1506 - 1510   2014年6月

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    記述言語:英語   出版者・発行元:WILEY-V C H VERLAG GMBH  

    A facile enantiospecific approach to (+)-ligudentatol (1) and (-)-ligudentatol (ent-1) is reported. The approach features the construction of a trisubstituted phenolic motif fused to a chiral aliphatic ring by a sequence of visible-light-mediated radical seleno transfer cyclization, bromination, concomitant selenoxide elimination-dehydrobromination, and demethoxycarbonylation, namely, a programmed aromatization. Biological evaluation of the enantiomers of ligudentatol obtained by the present route revealed for the first time their cytotoxicity towards various cancer cell lines.

    DOI: 10.1002/asia.201400110

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  • Endeavors to Access Molecular Complexity: Strategic Use of Free Radicals in Natural Product Synthesis

    Takehiko Yoshimitsu

    CHEMICAL RECORD   14 ( 2 )   268 - 279   2014年4月

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    記述言語:英語   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Free radicals, which in the past were considered unruly chemical species, have become manageable and indispensable for synthetic organic chemistry. The unique nature of free radicals has allowed practitioners in organic synthesis to design flexible approaches to produce various materials ranging from small molecules to polymers. The present Personal Account describes the author's endeavors to create molecular complexity by the strategic use of free radicals, with an emphasis on the synthesis of bioactive natural products.

    DOI: 10.1002/tcr.201300024

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  • A new route to platencin via decarboxylative radical cyclization

    Gamal A. I. Moustafa, Yuki Saku, Hiroshi Aoyama, Takehiko Yoshimitsu

    CHEMICAL COMMUNICATIONS   50 ( 99 )   15706 - 15709   2014年

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    記述言語:英語   出版者・発行元:ROYAL SOC CHEMISTRY  

    A new approach to platencin, a potent antibiotic isolated from Streptomyces platensis, has been established. The highly congested tricyclic core of the natural product was successfully constructed by decarboxylative radical cyclization of an alkynyl silyl ester with Pb(OAc)(4) in the presence of pyridine in refluxing 1,4-dioxane. The key decarboxylation, which likely takes place via lead(IV) esterification followed by carbon-centered radical generation and subsequent capture of the radical with a triple bond, allows the rapid construction of the twisted polycyclic system.

    DOI: 10.1039/c4cc07316a

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  • An integrated approach to the discovery of potent agelastatin A analogues for brain tumors: chemical synthesis and biological, physicochemical and CNS pharmacokinetic analyses

    Zhimin Li, Daisuke Shigeoka, Thomas R. Caulfield, Takashi Kawachi, Yushi Qiu, Takuma Kamon, Masayoshi Arai, Han W. Tun, Takehiko Yoshimitsu

    MEDCHEMCOMM   4 ( 7 )   1093 - 1098   2013年7月

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    記述言語:英語   出版者・発行元:ROYAL SOC CHEMISTRY  

    (-)-Agelastatin A (AA), isolated from the coral sea axinellid sponge Agelas dendromorpha, has shown a high antineoplastic activity. We have synthesized eighteen AA analogues and analyzed their cytotoxicities towards three cancer cell lines. By the structure-activity relationship (SAR) study, we identified three novel analogues with higher or comparable cytotoxic activities to AA. They were subjected to chemoinformatic analysis, which revealed physicochemical properties favoring excellent central nervous system (CNS) penetration. CNS pharmacokinetic analysis in murine models validated the chemoinformatic prediction and revealed that these analogues indeed had better CNS penetration than AA. These novel potent AA analogues deserve further evaluation for therapeutic use against cancers, particularly primary and secondary brain tumors.

    DOI: 10.1039/c3md00094j

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  • Formal synthesis of (-)-agelastatin A: an iron(II)-mediated cyclization strategy

    Daisuke Shigeoka, Takuma Kamon, Takehiko Yoshimitsu

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   9   860 - 865   2013年5月

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    記述言語:英語   出版者・発行元:BEILSTEIN-INSTITUT  

    An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (-)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N-iron intermediates in the redox states were operative.

    DOI: 10.3762/bjoc.9.99

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  • Structure-activity relationships of hybrid annonaceous acetogenins: Powerful growth inhibitory effects of their connecting groups between heterocycle and hydrophobic carbon chain bearing THF ring on human cancer cell lines

    Naoto Kojima, Tetsuya Fushimi, Takahiro Tatsukawa, Takehiko Yoshimitsu, Tetsuaki Tanaka, Takao Yamori, Shingo Dan, Hiroki Iwasaki, Masayuki Yamashita

    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY   63   833 - 839   2013年5月

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    記述言語:英語   出版者・発行元:ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER  

    Five novel hybrid molecules of annonaceous acetogenins and insecticides targeting mitochondrial complex I were synthesized and their growth inhibitory activities against 39 human cancer cell lines were investigated. It was revealed that the connecting group between the N-methylpyrazole part and the hydrophobic alkyl chain bearing the THF ring influenced their biological activities significantly. Amide-connected analog 2, in particular, showed selective and very potent activity (<10 nM) against some cancer cell lines. (C) 2013 Elsevier Masson SAS. All rights reserved.

    DOI: 10.1016/j.ejmech.2013.03.009

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  • Potent Growth Inhibitory Activity of (±)-Platencin towards Multi-Drug-Resistant and Extensively Drug-Resistant Mycobacterium tuberculosis

    Moustafa, G. A. I, Nojima, S, Yamano, Y, Aono, A, Arai, M, Mitarai, S, Tanaka, T, Yoshimitsu, T

    Med. Chem. Commun.   4 ( 4 )   720 - 723   2013年4月

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  • Dichlorination of olefins with NCS/Ph3P

    Yasumasa Kamada, Yuta Kitamura, Tetsuaki Tanaka, Takehiko Yoshimitsu

    ORGANIC & BIOMOLECULAR CHEMISTRY   11 ( 10 )   1598 - 1601   2013年

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    記述言語:英語   出版者・発行元:ROYAL SOC CHEMISTRY  

    A 2 : 1 mixture of NCS and Ph3P successfully promoted the anti-dichlorination of olefins to provide corresponding dichlorides, serving as a molecular chlorine surrogate generated in situ.

    DOI: 10.1039/c3ob27345h

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  • Double C-H Functionalization in Sequential Order: Direct Synthesis of Polycyclic Compounds by a Palladium-Catalyzed C-H Alkenylation-Arylation Cascade

    Hiroaki Ohno, Mutsumi Iuchi, Naoto Kojima, Takehiko Yoshimitsu, Nobutaka Fujii, Tetsuaki Tanaka

    CHEMISTRY-A EUROPEAN JOURNAL   18 ( 17 )   5352 - 5360   2012年4月

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    記述言語:英語   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Palladium-catalyzed cascade C?H alkenylation and arylation provides convenient access to polycyclic aromatic compounds. Treatment of 3-bromoaniline derivatives bearing a bromocinnamyl group on the nitrogen atom with a catalytic amount of [Pd(OAc)2] and PCy3 center dot HBF4 in the presence of Cs2CO3 in dioxane affords naphthalene-fused indole derivatives in good yields. This double cyclization reaction is also applicable to heterocyclic substrates, giving fused indoles containing a heteroaromatic ring such as dibenzofuran, dibenzothiophene, carbazole, indole, or benzofuran through heterocyclic C-H arylation. When using a 2,6-unsubstituted aniline derivative, the first C-H arylation preferentially proceeds at the more hindered position of the aniline ring.

    DOI: 10.1002/chem.201103819

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  • Pharmacokinetics of Agelastatin A in the central nervous system

    Zhimin Li, Takuma Kamon, David A. Personett, Thomas Caulfield, John A. Copland, Takehiko Yoshimitsu, Han W. Tun

    MEDCHEMCOMM   3 ( 2 )   233 - 237   2012年2月

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    記述言語:英語   出版者・発行元:ROYAL SOC CHEMISTRY  

    Agelastatin A (AA) is an anti-neoplastic agent with anti-osteopontin (OPN) activity. Brain tumors often express OPN significantly. A comprehensive chemoinformatic analysis followed by in vivo pharmacokinetic evaluations in mice is performed. CNS penetration of AA is about 10%. AA should be further tested for activity against brain tumors.

    DOI: 10.1039/c1md00240f

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  • Stereoselective α-Quaternization of 3-Methoxycycloalk-2-enones via 1,4-Diastereoinduction of Alkoxy Dienolates

    Moustafa, G. A. I, Kamada, Y, Tanaka, T, Yoshimitsu, T

    J. Org. Chem.   77 ( 2 )   1202 - 1207   2012年1月

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  • Stereoconvergent route to chiral cyclohexenone building blocks: formal synthesis of (-)-dysidiolide

    Gamal A. I. Moustafa, Yasumasa Kamada, Tetsuaki Tanaka, Takehiko Yoshimitsu

    ORGANIC & BIOMOLECULAR CHEMISTRY   10 ( 43 )   8609 - 8615   2012年

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    記述言語:英語   出版者・発行元:ROYAL SOC CHEMISTRY  

    A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3'-Hydroxy-4'-methylpent-4'-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.

    DOI: 10.1039/c2ob26532j

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  • Intramolecular iron(II)-catalyzed aminobromination of allyl N-tosyloxycarbamates

    Takuma Kamon, Daisuke Shigeoka, Tetsuaki Tanaka, Takehiko Yoshimitsu

    ORGANIC & BIOMOLECULAR CHEMISTRY   10 ( 12 )   2363 - 2365   2012年

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    記述言語:英語   出版者・発行元:ROYAL SOC CHEMISTRY  

    Allyl N-tosyloxycarbamates are found to be catalytically transformed into beta-brominated oxazolidinones with FeBr2/n-Bu4NBr in t-BuOH.

    DOI: 10.1039/c2ob07190h

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  • Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines

    Naoto Kojima, Yuki Suga, Hiromi Hayashi, Takao Yamori, Takehiko Yoshimitsu, Tetsuaki Tanaka

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   21 ( 19 )   5745 - 5749   2011年10月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The convergent synthesis of C35-fluorinated analogues of solamin, a mono-THF Annonaceous acetogenin, has been achieved by the Sonogashira coupling of the THF ring fragment and the fluorinated gamma-lactone fragment. It was revealed that the number of fluorine atoms on the gamma-lactone moiety affects the growth inhibitory activities against human cancer cell lines. (C) 2011 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2011.08.011

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  • Total Synthesis of (±)-Platencin

    Yoshimitsu, T, Nojima, S, Hashimoto, M, Tanaka, T

    Org. Lett.   13 ( 14 )   3698 - 3701   2011年7月

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  • Total Synthesis of (±)-Kainic Acid: A Photochemical C–H Carbamoylation Approach

    Kamon, T, Irifune, Y, Tanaka, T, Yoshimitsu, T

    Org. Lett.   13 ( 10 )   2674 - 2677   2011年5月

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  • Asymmetric Total Synthesis of (+)-Danicalipin A

    Takehiko Yoshimitsu, Ryo Nakatani, Akihiro Kobayashi, Tetsuaki Tanaka

    ORGANIC LETTERS   13 ( 5 )   908 - 911   2011年3月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    A convergent asymmetric total synthesis of (+)-danicalipin A is accomplished, in which two chlorinated fragments are stereoselectively joined by 1,3-dipolar coupling, leading to the confirmation of the absolute configuration of the natural product.

    DOI: 10.1021/ol1029518

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  • Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution

    Naoto Kojima, Takekuni Morioka, Daisuke Urabe, Masahiro Yano, Yuki Suga, Naoyoshi Maezaki, Ayako Ohashi-Kobayashi, Yasuyuki Fujimoto, Masatomo Maeda, Takao Yamori, Takehiko Yoshimitsu, Tetsuaki Tanaka

    BIOORGANIC & MEDICINAL CHEMISTRY   18 ( 24 )   8630 - 8641   2010年12月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The convergent synthesis of fluorescence-labeled solamin, an antitumor Annonaceous acetogenin, was accomplished by two asymmetric alkynylations of 2,5-diformyl tetrahydrofuran with an alkyne tagged with fluorescent groups and another alkyne with an alpha,beta-unsaturated gamma-lactone. Assay for the growth inhibitory activity against human cancer cell lines revealed that the probe with the fluorescent groups at the end of the hydrocarbon chain may have the same mode of action as natural acetogenins. The merged fluorescence of dansyl-labeled solamin and MitoTracker Red suggests that Annonaceous acetogenins localize in the mitochondria. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmc.2010.10.004

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  • Asymmetric Total Synthesis of (+)-Hexachlorosulfolipid, a Cytotoxin Isolated from Adriatic Mussels

    Takehiko Yoshimitsu, Naoya Fukumoto, Ryo Nakatani, Naoto Kojima, Tetsuaki Tanaka

    JOURNAL OF ORGANIC CHEMISTRY   75 ( 16 )   5425 - 5437   2010年8月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    The enantioselective total synthesis of (+)-hexachlorosulfolipid, a cytotoxin found in the Adriatic mussel Mytilus galloprovincialis, is described. The unique chlorinated hydrocarbon motif of the lipid is successfully furnished by a series of dichlorination reactions of chiral epoxides with chlorophosphonium reagent generated in situ from Ph(3)P/NCS. The present total synthesis has allowed the confirmation of the absolute configuration of the natural cytotoxic (+)-hexachlorosulfolipid originally proposed by Fattorusso, Ciminiello, and co-workers.

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  • Studies of the Asymmetric Total Synthesis of Clavilactone D by the 'Lariat' Cyclization Strategy

    Takehiko Yoshimitsu, Shoji Nojima, Masashi Hashimoto, Koji Tsukamoto, Tetsuaki Tanaka

    SYNTHESIS-STUTTGART   17 ( 17 )   2963 - 2969   2009年9月

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    記述言語:英語   出版者・発行元:GEORG THIEME VERLAG KG  

    A route to the core structure of clavilactone D, a new member of the tyrosine kinase inhibitors, is reported. The route employs sequential cyclization initiated by iodo etherification followed by Friedel-Crafts cyclization to furnish a polycyclic lactone fused with an aromatic ring, which is readily transformed into the proposed clavilactone scaffold.

    DOI: 10.1055/s-0029-1216909

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  • Total Synthesis of the β-Catenin Inhibitor, (-)-Agelastatin A: A Second-Generation Approach Based on Radical Aminobromination

    T.Yoshimitsu, T. Ino, N. Futamura, T. Kamon, T. Tanaka

    Org. Lett.   11 ( 15 )   3402 - 3405   2009年8月

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  • SYNTHESIS OF CHAETOMELLIC ANHYDRIDE A, A POTENT INHIBITOR OF RAS PROTEIN FARNESYLTRANSFERASE

    Takehiko Yoshimitsu, Yoshimasa Arano, Tomohiro Kaji, Tatsunori Ino, Hiroto Nagaoka, Tetsuaki Tanaka

    HETEROCYCLES   77 ( 1 )   179 - 186   2009年1月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Chaetomellic anhydride A, a potent inhibitor of Ras protein farnesyltransferase, was synthesized in 61% yield over four steps from methyl propionate. The synthesis features palladium-catalyzed carboxylation reaction under Cacchi conditions, efficiently incorporating carbon monoxide generated in situ from acetic formic anhydride into beta-carbomethoxyalkenyl triflate, and giving rise to the maleic anhydride motif of chaetomellic anhydride A. Noteworthy is the remarkable reactivity of the carboxylation reaction that takes place at room temperature despite the fact that common palladium-catalyzed carboxylations generally require rather harsh conditions. The scope of the method is also presented.

    DOI: 10.3987/COM-08-S(F)16

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  • Enantiocontrolled Synthesis of Polychlorinated Hydrocarbon Motifs: A Nucleophilic Multiple Chlorination Process Revisited

    Takehiko Yoshimitsu, Naoya Fukumoto, Tetsuaki Tanaka

    JOURNAL OF ORGANIC CHEMISTRY   74 ( 2 )   696 - 702   2009年1月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    Polychlorinated hydrocarbon motifs have been synthesized in enantiomerically pure forms by means of nucleophilic multiple chlorinations of chiral epoxides, which stereospecifically incorporate halogen atoms into oxygenated molecular scaffolds. The present study demonstrates the scope of the N-chlorosuccinimide (NCS)/organophosphine reagent system that forms multiple sp(3)C-Cl bonds in a regularly repeating pattern, with proper stereochemical configurations and evaluates its applicability to various epoxides having elaborate structures. It is noteworthy that tetrachlorinated motifs are produced in one step from bisepoxides by using NCS/Ph(3)P. Furthermore, Ph(2)PCl used in combination with NCS has been found to serve as a potentially useful alternative to NCS/Ph(3)P, especially for promoting dichlorination reactions of alkenyl-substituted epoxides.

    DOI: 10.1021/jo802093d

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  • Total Synthesis of (-)-Agelastatin A

    Takehiko Yoshimitsu, Tatsunori Ino, Tetsuaki Tanaka

    ORGANIC LETTERS   10 ( 23 )   5457 - 5460   2008年12月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    A new route to (-)-agelastatin A is reported. The requisite nitrogen functionalities of the agelastatin core have been installed by intramolecular aziridination of an azidoformate and subsequent regioselective azidation, leading to net trans-diamination of the double bond. The present synthesis also demonstrates two new protocols for the preparation of an imidazolidinone hemiaminal motif from an oxazolidinone intermediate which comprise sequential N-tert-butoxycarbonylation, urea formation, hydrolysis, and oxidative cyclization, and direct aminolysis and subsequent oxidative cyclization.

    DOI: 10.1021/ol802225g

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  • Synthesis of (±)-Aphanorphine: a New Approach to Tricyclic 3-Benzazepine Scaffold Using Two Radical C-C Bond-Forming Reactions

    Yoshimitsu, T, Atsumi, C, Iimori, E, Nagaoka, H, Tanaka, T

    Tetrahedron Lett.   49 ( 29-30 )   4473 - 4475   2008年7月

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  • フリーラジカルが拓くヘテロ分子骨格形成の新手法

    好光健彦, 田中徹明

    生産と技術   90   99 - 101   2008年

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  • Radical fixation of functionalized carbon resources: alpha-sp(3)C-H carbamoylation of tertiary amines with aryl isocyanates

    Takehiko Yoshimitsu, Kenichi Matsuda, Hiroto Nagaoka, Koji Tsukamoto, Tetsuaki Tanaka

    ORGANIC LETTERS   9 ( 24 )   5115 - 5118   2007年11月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    A new carbamoylation of tertiary amines is reported. This rare C-H transformation features the direct generation of alpha-aminoalkyl radicals from tertiary amines, followed by the addition of the resultant nucleophilic radicals to isocyanates, enabling unique access to N,N-dlalkylated amino acid derivatives. The authors put forward a mechanistic proposal that is based on the isolation of borinamides produced by capturing nitrogen radical intermediates with Et3B. The present transformation provides a novel one-step process for producing mepivacaine, a clinically important local anesthetic, from readily available materials.

    DOI: 10.1021/ol7023295

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  • フリーラジカルによるα-ヘテロ原子置換sp3炭素―水素結合の新変換法の発見と進展

    好光健彦

    ファルマシア‐最前線‐   43 ( 3 )   219 - 223   2007年

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    記述言語:日本語   出版者・発行元:公益社団法人日本薬学会  

    CiNii Article

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  • 高反応性ラジカル種が誘起する炭素-炭素および炭素-水素結合変換と生物活性物質合成への活用

    好光健彦, 長岡博人, 田中徹明

    有機合成化学協会誌   65   665 - 676   2007年

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  • 解説「Barton反応」

    好光健彦

    有機合成化学協会誌   65   727 - 727   2007年

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  • Radical hydroxyalkylation of C-H bond adjacent to nitrogen of tertiary amides, ureas, and amines

    T Yoshimitsu, Y Arano, H Nagaoka

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   127 ( 33 )   11610 - 11611   2005年8月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/ja053855q

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  • Radical alpha-C-H hydroxyalkylation of ethers and acetal

    T Yoshimitsu, Y Arano, H Nagaoka

    JOURNAL OF ORGANIC CHEMISTRY   70 ( 6 )   2342 - 2345   2005年3月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    Ethers and an acetal were found to undergo direct intermolecular addition to aldehydes under the Et3B/air conditions. This study presents a very unique and simple means for the radical alpha-C-H hydroxyalkylation of oxygen-containing compounds.

    DOI: 10.1021/jo048248k

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  • Studies on the total synthesis of (-)-CP-263,114

    T Yoshimitsu, S Sasaki, Y Arano, H Nagaoka

    JOURNAL OF ORGANIC CHEMISTRY   69 ( 26 )   9262 - 9268   2004年12月

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    記述言語:英語   掲載種別:書評論文,書評,文献紹介等   出版者・発行元:AMER CHEMICAL SOC  

    Alkoxyl radicals have a wide range of applications in organic synthesis due to their remarkable chemical properties in molecular transformation. The present study shows two types of alkoxyl radicals (primary vs tertiary) to selectively undergo dehydrogenation and beta-scission to give rise to key structural elements of (-)-CP-263,114 (1). By alkoxyl radical transformation followed by installation of the C19-C25 (CP numbering) side chain and the bridged bisacetal unit, the functionalized CP precursor 2 was obtained.

    DOI: 10.1021/jo048681u

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  • Total synthesis of (+)-muconin

    T Yoshimitsu, T Makino, H Nagaoka

    JOURNAL OF ORGANIC CHEMISTRY   69 ( 6 )   1993 - 1998   2004年3月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    (+)-Muconin (1), isolated from the leaves of Rollinia mucosa (Jacq.) Baill. (Annonaceae), is a sequential THF/THP-possessing acetogenin that exhibits potent and selective in vitro cytotoxicity toward pancreatic and breast tumor cell lines. In this study, a new route was established for obtaining (+)-muconin (1) starting with (-)-muricatacin (2), a compound recently synthesized via the novel alpha-C-H hydroxyalkylation and alpha'-C-H oxidation of tetrahydrofuran.

    DOI: 10.1021/jo0303721

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  • Synthesis of (-)-muricatacin via alpha- and alpha '-C-H bond functionalization of tetrahydrofuran

    T Yoshimitsu, T Makino, H Nagaoka

    JOURNAL OF ORGANIC CHEMISTRY   68 ( 19 )   7548 - 7550   2003年9月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    (-)-Muricatacin, a potent cytotoxic (4R,5R)-5-hydroxyheptadecan-4-olide, has been synthesized through alpha-C-H hydroxyalkylation and alpha'-C-H oxidation of tetrahydrofaran. This study presents a novel method for C-H bond functionalization as a means for preparing gamma-(hydroxyalkyl)-gamma-butyrolactones.

    DOI: 10.1021/jo0301696

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  • Hydroxyalkylation of alpha-C-H bonds of tetrahydrofuran with aldehydes in the presence of triethylborane and tert-butyl hydroperoxide

    T Yoshimitsu, Y Arano, H Nagaoka

    JOURNAL OF ORGANIC CHEMISTRY   68 ( 2 )   625 - 627   2003年1月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    The alpha-hydroxyalkylation of tetrahydrofuran with aldehydes via radical C-H abstraction was conducted using triethylborane in the presence of tert-butyl hydroperoxide. This study presents a rare instance of direct intermolecular radical addition of unactivated cyclic ether to aldehydes.

    DOI: 10.1021/jo020590e

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  • Synthesis of the CD ring system of paclitaxel by atom-transfer radical annulation reaction

    T Yoshimitsu, H Nakajima, H Nagaoka

    TETRAHEDRON LETTERS   43 ( 47 )   8587 - 8590   2002年11月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Atom-transfer radical annulation of diene derived from D-glucose under Kharasch conditions provided access to the fully functionalized CD ring system of paclitaxel. (C) 2002 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(02)02058-0

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  • Asymmetric synthesis of the core structure of (-)-CP-263,114

    T Yoshimitsu, S Yanagisawa, H Nagaoka

    ORGANIC LETTERS   2 ( 23 )   3751 - 3754   2000年11月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    [GRAPHICS]
    The enantioselective construction of a fully functionalized core structure of (-)-CP-263,114 (1) containing most of the required functionality for total synthesis, was conducted through sequential radical fragmentation-reductive olefination.

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  • New Route to the Synthesis of the Illudane Skeleton by Michael–Michael-Elimination Reaction

    Tokuzaki, K, Kanemitsu, Y, Yoshimitsu, T, Nagaoka, H

    Tetrahedron Lett.   41 ( 31 )   5923 - 5926   2000年7月

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  • New method for the synthesis of alpha-substituted tetrahydrofuran-2-methanols through diastereoselective addition of THF to aldehydes mediated by Et3B in the presence of air

    T Yoshimitsu, M Tsunoda, H Nagaoka

    CHEMICAL COMMUNICATIONS   ( 17 )   1745 - 1746   1999年9月

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    記述言語:英語   出版者・発行元:ROYAL SOC CHEMISTRY  

    The tetrahydrofuranyl radical, generated from THF with Et3B in the presence of air, was found to react with aldehydes threo-selectively to afford alpha-substituted tetrahydrofuran-2-methanols, the common structural motifs of biologically active acetogenin polyketides, in moderate yields.

    DOI: 10.1039/A904745J

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  • An approach to the synthesis of CP-263,114: complementary routes to the bicyclic ring system via two kinds of fragmentation reaction

    T Yoshimitsu, M Yanagiya, H Nagaoka

    TETRAHEDRON LETTERS   40 ( 28 )   5215 - 5218   1999年7月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Two complementary methods for the construction of the ring system of CP-263,114 (1), one relying on the Grob fragmentation reaction and the other on a sequential photolytic alkoxy radical fragmentation-reduction, are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(99)00941-7

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  • A new synthetic route for construction of the core of zaragozic acids

    H Koshimizu, T Baba, T Yoshimitsu, H Nagaoka

    TETRAHEDRON LETTERS   40 ( 14 )   2777 - 2780   1999年4月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    A new synthetic route for construction of the core moiety of zaragozic acids from 2,5-furandimethanol (2) is described. This synthesis involves highly stereocontrolled transformation of 2 into 7-oxabicyclo[2.2.1] heptane derivative 13, and the Grob fragmentation-reduction-iodo acetalization reaction (one-pot process) of 13 as a key step to give 16. (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(99)00256-7

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  • Application of newly developed anti-selective aldol methodology: Synthesis of C6-C13 and C19-C28 fragments of miyakolide

    T Yoshimitsu, JJ Song, GQ Wang, S Masamune

    JOURNAL OF ORGANIC CHEMISTRY   62 ( 26 )   8978 - 8979   1997年12月

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    記述言語:英語   掲載種別:速報,短報,研究ノート等(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/jo971863m

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受賞

  • 大阪大学総長による表彰

    2014年  

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    受賞国:日本国

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  • Presidential Awards for Excellence (Osaka University)

    2014年  

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  • The Society of Synthetic Organic Chemistry, Japan. The 11th Kansai Branch Award

    2013年  

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  • 第11回 有機合成化学協会関西支部賞

    2013年  

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    受賞国:日本国

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  • アジア最先端有機化学国際会議 Asian Core Program (ACP) Lectureship Award (Singapore)

    2013年  

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  • アジア最先端有機化学国際会議 Asian Core Program (ACP) Lectureship Award (Thailand)

    2008年  

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▼全件表示

 

担当授業科目

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  • 創薬有機化学I (2020年度) 特別  - その他

  • 創薬有機化学II (2020年度) 特別  - その他

  • 医薬化学3 (2020年度) 第3学期  - 金1,金2

  • 医薬化学3 (2020年度) 第3学期  - 金1,金2

  • 医薬化学II(構造生物学を含む。) (2020年度) 1~3学期  - [第1学期]木1,木2, [第2学期]金1,金2, [第3学期]金1,金2

  • 有機化学・天然物化学 (2020年度) 特別  - その他

  • 有機化学5 (2020年度) 第1学期  - 水1,水2

  • 有機化学5 (2020年度) 第1学期  - 水1,水2

  • 有機化学6 (2020年度) 第2学期  - 水1,水2

  • 有機化学6 (2020年度) 第2学期  - 水1,水2

  • 有機化学IV (2020年度) 1・2学期  - 水1,水2

  • 有機化学IV (2020年度) 1・2学期  - 水1,水2

  • 薬学基礎実習Ⅱ (2020年度) 特別  - その他

  • 薬学基礎実習Ⅱ (2020年度) 特別  - その他

▼全件表示