Bicyclo [3. 3. 1]nonanes as Synthetic Intermediates. IV. Behavior of Bicyclo [3. n. 1] alkan-3-ones toward the Baeyer-Villiger Oxidation

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概要

• 論文の詳細を見る

• The Baeyer-Villiger oxidation of bicyclo [3. n. 1] alkan-3-ones and related systems is described. Bicyclo [3. 3. 1] nonan-2-one (8) was oxidized into the corresponding lactone, which was found to be converted into the cis-1,3-disubstituted cyclohexane system by the subsequent methanolysis. Meanwhile, the 3-oxo system (2) manifested an anomalous inactivity against the oxidation. The"backside steric hindrance"caused by the axial (endo) proton at C-7 was postulated as the origin of the inactivity. The differential reactivity of the ketones in the Baeyer-Villiger reaction of the bicyclic systems (2,3,4) enabled the regiospecific lactonization of the bicyclic diketones (17,18,19) into the lactones (37,38,39), which would be important precursors for specifically substituted medium-sized lactones, to be achieved.

• 社団法人日本薬学会の論文
• 1979-01-25

著者

• 村岡 修

  Faculty of Pharmaceutical Sciences, Kinki University

• 村岡 修

  Faculty Of Pharmaceutical Sciences Kinki University

• 百瀬 雄章

  Faculty of Pharmaceutical Sciences, Kinki University

• 百瀬 雄章

  富山医薬大・薬

• 新子 省悟

  Exploratory Research Laboratories I, Daiichi Pharmaceutical Co., Ltd.,

• 百瀬 雄章

  (present Address)faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Osaka University

• 新子 省悟

  Faculty of Pharmaceutical Sciences, Osaka University

• 堀田 多美子

  Faculty of Pharmaceutical Sciences, Osaka University

• 新子 省悟

  Exploratory Research Laboratories I Daiichi Pharmaceutical Co. Ltd.

• 堀田 多美子

  Faculty Of Pharmaceutical Sciences Osaka University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Muraoka O

  Shonai Regional Center For Plant Biotechnol. Yamagata

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