16 Spirovetivane型Phytoalexin類の合成研究 : (±)-Lubiminolおよび(±)-oxylubiminの立体選択的全合成

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概要

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• As one of continuous synthetic studies on naturally occurring spiro compounds, we describe stereoselective total synthesis of the hydroxylated spirovetivane-type phytoalxins, lubiminol (2) and oxylubimin (4) in racemic form. 1. Total Synthesis of (±)-Lubiminol (2) The previously reported spiro-enone (8) was transformed into 14 via 13 by a several-steps sequence. The three-carbon unit introduction at C-2 in 14 was followed by catalytic hydrogenation to give 9 as a single diastereoiosmer, which was converted into (±)-lubiminol (2). 2. A New Method for α'-Hydroxylation of α,β-Unsaturated Ketones We have developed a novel method for introduction of hydroxyl group to the α'-position of α,β-unsaturated ketones by means of TPPO oxidation of their silyl enol ethers. 3. Total Synthesis of (±)-Oxylubimin (±)-Oxylubimin (4), the highest oxidized spirovetivane-type phytoalexin, was also totally synthesized with high stereoselectivity usig the above mentioned hydroxylation method as a crucial step starting the enone (8).

• 天然有機化合物討論会の論文
• 1985-09-07

著者

• 山田 稔

  Faculty Of Pharmaceutical Sciences Osaka University

• 竹本 佳司

  Faculty Of Pharmaceutical Sciences Osaka University

• 岩田 宙造

  阪大・薬

• 黒田 武志

  阪大・薬

• 今西 武

  阪大・薬

• 田中 徹明

  阪大・薬

• 内田 秀治

  Faculty of Pharmaceutical Sciences, Osaka University

• 田中 徹明

  阪大院薬

• 中村 文胤

  日本新薬(株)知的財産部調査課

• Tanaka T

  Kvushu Univ. Fukuoka Jpn

• Tanaka T

  Osaka Univ. Osaka Jpn

• Takemoto Yoshiji

  Faculty Of Pharmaceutical Sciences Osaka University

• Takemoto Y

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Kuroda T

  Faculty Of Pharmaceutical Sciences Osaka University

• Kuroda Takeshi

  Faculty Of Pharmaceutical Sciences Fukuoka University

• 窪田 均

  Faculty Of Pharmaceutical Sciences Osaka University

• 竹本 佳司

  阪大・薬

• 窪田 均

  阪大・薬

• 中村 文胤

  阪大・薬

• 山田 稔

  阪大・薬

• 内田 秀治

  阪大・薬

• 中村 文胤

  田辺製薬 研究企画部

• 中村 文胤

  Faculty Of Pharmaceutical Sciences Osaka University

• 中村 文胤

  日本新薬(株)創薬研究所

• 内田 秀治

  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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