Synthetic Studies on Aphidicolane and Stemodane Diterpenes. IV.A Stereoselective Formal Total Synthesis of (±)-Aphidicolin

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概要

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• A formal total synthesis of (±)-aphidicolin (1) was accomplished starting from the tricyclic ketone (2)corresponding to the B/C/D ring system. The quaternary carbon center adjacent to the spirocarbon was constructed stereoselectively by conjugate addition of a methyl group to the enone (7) obtained from 2 in a four-step sequence.The tetracyclic enone (3) was obtained via acid-catalyzed intramolecular aldol condensation of the tricarbonyl compound (10) followed by 1,3-carbonyl transposition, in which Pd(0)-catalyzed reductive deacetoxylation of γ-acetoxy-α, β-enone (15) was a crucial step. The A-ring manipulation was performed by a similar procedure to the Ireland method to give the keto-acetonide (4), a degradation product of 1,which has already been efficiently reconverted to 1.

• 社団法人日本薬学会の論文
• 1995-02-15

著者

• 金 相元

  Faculty of Pharmaceutical Sciences, Josai University

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 井上 哲也

  Faculty Of Pharmaceutical Sciences Osaka University

• 田中 徹明

  Faculty of Pharmaceutical Sciences, Osaka University

• 村上 和夫

  Faculty of Pharmaceutical Sciences, Osaka University

• 奥田 修

  Faculty of Pharmaceutical Sciences, Osaka University

• 黒田 武志

  Faculty of Pharmaceutical Sciences, Osaka University

• 亀位 勝秀

  Faculty of Pharmaceutical Sciences, Osaka University

• 村田 隆史

  Faculty of Pharmaceutical Sciences, Osaka University

• 吉野 仁

  Faculty of Pharmaceutical Sciences, Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 村上 和夫

  阪大院薬

• 金 相元

  Faculty Of Pharmaceutical Sciences Josai University

• 黒田 武志

  Faculty Of Pharmaceutical Sciences Osaka University

• 村田 隆史

  阪大院薬

• 吉野 仁

  阪大院薬

• 岩田 宙造

  阪大院薬

• 田中 徹明

  阪大院薬

• 田中 徹明

  Faculty Of Pharmaceutical Sciences Osaka University

• Tanaka T

  Kvushu Univ. Fukuoka Jpn

• Tanaka T

  Osaka Univ. Osaka Jpn

• Kim S‐w

  Faculty Of Pharmaceutical Sciences Josai University

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• Inoue T

  Ohmiya Research Laboratory Fuji Yakuhin Co. Ltd

• Kuroda T

  Faculty Of Pharmaceutical Sciences Osaka University

• 田中 恒雄

  Department Of Pharmacy Hyogo College Of Medicine

• Tanaka Tetsuaki

  Faculty Of Pharmaceutical Sciences Osaka University

• Yamashita Haruhisa

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 吉野 仁

  Faculty Of Pharmaceutical Sciences Osaka University

• Mimura T

  New Product Research Laboratories Ii Daiichi Pharmaceutical Company Ltd.

• Okuda O

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 奥田 修

  Faculty Of Pharmaceutical Sciences Osaka University

• Inoue T

  Osaka University Of Pharmaceutical Sciences

• 井上 輝比古

  Pharmaceutical Research Department Ube Laboratory Corporate Research & Development Ube Industrie

• Murakami K

  Osaka Univ. Osaka Jpn

• 亀位 勝秀

  Faculty Of Pharmaceutical Sciences Osaka University

• Murakami K

  阪大院薬

• Inoue Takao

  Faculty Of Pharmaceutical Sciences Hoshi University

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