39 Pseudoguaianolidesの合成研究 : (±)-Carpesiolinの全合成

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概要

• 論文の詳細を見る

• A total synthesis of (±)-carpesiolin (1), an antibiotic substance, is described along a new, efficient and straightforward route to this class of sesquiterpenoides (pseudoguaianolides). This route features on the following three points: 1) the stereochemically defined introduction of C_<10> (pseudoguaianolide numbering) methyl group in a-orientation, 2) the regiospecific ring expansion reaction leading to the trans-perhydroazulenone skeleton, and 3) the complete stereo-control of other chiralities (C_6-C_8) on the 7-membered ring. The severe 1,3-diaxial interaction in the β-methyl ketone (4) caused a complete isomerization to its α-methyl isomer (3), which was ring-expanded regiospecifically to the perhydroazulenone (7). The ketone 7 was converted to the γ-lactone (16) in 5 steps, whose trifluoroacetate (17) on treatment with an acid was transformed into the alcohol (18) via an unexpected intramolecular acyl migration. The title compound 1 was synthesized in further 7 steps from 18. Application of this methodology to other pseudoguaianolides is in progress.

• 天然有機化合物討論会の論文
• 1981-09-10

著者

• 長尾 恵四郎

  Faculty of Pharmaceutical Sciences, Josai University

• 吉村 磯孝

  Faculty of Pharmaceutical Sciences, Josai University

• 金 相元

  Faculty Of Pharmaceutical Sciences Josai University

• Kim S‐w

  Faculty Of Pharmaceutical Sciences Josai University

• 金 相元

  城西大薬

• 吉村 磯孝

  Faculty Of Pharmaceutical Sciences Josai University

• 長尾 恵四郎

  Faculty Of Pharmaceutical Sciences Josai University

• 千葉 昌人

  Faculty Of Pharmaceutical Sciences Josai University

• 長尾 恵四郎

  城西大薬

• 千葉 昌人

  城西大薬

• 吉村 磯孝

  城西大薬

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