Regioselective Synthesis of 14-Membered Biaryl Ethers : Total Synthesis of RA-VII and Deoxybouvardin

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概要

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• In order to obtain a key compound (22a") for synthesis of RA-VII (1) and deoxybouvardin (2), construction of the 14-membered ring system was performed by means of thallium trinitrate-mediated oxidation of the tetrahalogeno amides 5-7. The dibromo dichloro amide 6 or the bromo trichloro amide 7 gave a natural type of 14-membered ring dienone (23a or 23c), whereas the tetrabromo amide 5 gave an unnatural type of product, 19a. The formation of the latter product 19a could be understood on the basis of energy calculations on plausible intermediates 26a-c and 27a-c in the transition state in the oxidaive coupling reaction. Compound 23a was further converted to 22a" through conventional procedures (aromatization; methylation; catalytic hydrogenation). This intermediate was readily converted to 1 and 2. Thus, total synthesis of RA-VII (1) and deoxybouvardin (2) was achieved for the first time.

• 公益社団法人日本薬学会の論文
• 1995-08-15

著者

• 星野 修

  東京理科大学薬学部

• 原 博

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• 原 博

  東京理科大学薬学部

• 井上 哲也

  Faculty Of Pharmaceutical Sciences Osaka University

• 竹谷 孝一

  東京都立衛生研究所

• 糸川 秀治

  Tokyo College Of Pharmacy

• 竹谷 孝一

  東京薬大薬

• 星野 修

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• 糸川 秀治

  東京薬科大学 薬学部

• 井上 勗

  Ohmiya Research Laboratory Fuji Yakuhin Co. Ltd.

• Inoue T

  Ohmiya Research Laboratory Fuji Yakuhin Co. Ltd

• 梅沢 勲

  Ohmiya Research Laboratory Fuji Yakuhin Co. Ltd.

• 湯浅 雅之

  Pola R & D Laboratory

• 原 博

  東京理大 薬

• 稲葉 隆之

  Central Pharmaceutical Research Institute, Japan Tabaco Inc.,

• 小倉 克之

  Department of Synthetic Chemistry, Faculty of Engineering, Chiba University

• 小松 克一郎

  Simulation Technology Inc.,

• Inoue T

  Osaka University Of Pharmaceutical Sciences

• 井上 輝比古

  Pharmaceutical Research Department Ube Laboratory Corporate Research & Development Ube Industrie

• 稲葉 隆之

  Central Pharmaceutical Research Institute Japan Tabaco Inc.

• 小倉 克之

  千葉大学工学部

• 星野 修

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• 小松 克一郎

  Simulation Technology Inc.

• Inoue Takao

  Faculty Of Pharmaceutical Sciences Hoshi University

• 糸川 秀治

  東京薬科大学

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