Synthetic Studies on Spirovetivane Phytoalexins. V. : A Stereoselective Total Synthesis of (±)-Oxylubimin

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概要

• 論文の詳細を見る

• (±)-Oxylubimin (4), the most highly oxygenated spirovetivane phytoalexin, was synthesized stereoselectively from a key intermediate, (2RS, 5RS, 9SR, 10RS)-9-hydroxy-6,10-dimethyl-2-pivaloyloxyspiro[4.5]dec-6-en-8-one (3). Its methoxymethyl ether (8) was reduced with NaBH_4 and CeCl_3・7H_2O to give predominantly the desired alcohol (9a) (9a/9b=6.4). The alcohol (9a) was successfully transformed into oxylubimin (4) via several steps, involving introduction of a bis(ethoxycarbonyl)methyl group at the C_2,catalytic hydrogenation of the C_6-C_7 double bond, and pyridinium chlorochromate oxidation of the hydroxymethyl group at C_6.

• 公益社団法人日本薬学会の論文
• 1990-02-25

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 竹本 佳司

  Faculty Of Pharmaceutical Sciences Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 黒田 武志

  Faculty Of Pharmaceutical Sciences Osaka University

• 今西 武

  大阪大学大学院薬学研究科

• 岩田 宙造

  阪大院薬

• Takemoto Yoshiji

  Faculty Of Pharmaceutical Sciences Osaka University

• Takemoto Y

  Graduate School Of Pharmaceutical Sciences Kyoto University

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• Kuroda Takeshi

  Faculty Of Pharmaceutical Sciences Fukuoka University

• 窪田 均

  Faculty Of Pharmaceutical Sciences Osaka University

• Kuroda T

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Imamura T

  Faculty Of Pharmaceutical Sciences Osaka University

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