7,7-Dimethyltricyclo[3.3.0.0^<2,8>]octan-3-ones as Synthetic Intermediates. II. : A Total Synthesis of (±)-Pentalenene, an Angular Triquinane Sesquiterpene

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概要

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• A total synthesis of (±)-pentalenene (3), one of the least-oxidized triquinane sesquiterpenes, is described. By a several-step sequence, 4,4-dimethyl-2-cyclopentenone (5) was derived to a tricyclooctanone (4), which was subjected to a reductive C_2-C_8 bond opening reaction to give 15. The triquinane derivative (20), obtained from 15,was transformed to (±)-pentalenene (3) and (±)-epi-pentalenene (21) in a 1.8 : 1 ratio.On the other hand, hydroboration-oxidation of 4 followed by tosylation gave easily separable products, 23 and 24,which were transformed to 20A and 20B, precuesors for (±)-3 and (±)-21,respectively.

• 公益社団法人日本薬学会の論文
• 1988-04-25

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 田中 徹明

  Faculty of Pharmaceutical Sciences, Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 田中 徹明

  阪大院薬

• 田中 徹明

  Faculty Of Pharmaceutical Sciences Osaka University

• Tanaka T

  Kvushu Univ. Fukuoka Jpn

• 山下 正行

  Faculty of Pharmaceutical Sciences, Osaka University

• Tanaka T

  Osaka Univ. Osaka Jpn

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• 仁張 総子

  Faculty of Pharmaceutical Sciences, Osaka University

• Imamura T

  Faculty Of Pharmaceutical Sciences Osaka University

• 山下 正行

  Faculty Of Pharmaceutical Sciences Osaka University

• 仁張 総子

  Faculty Of Pharmaceutical Sciences Osaka University

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