Bicyclo [3.3.1] nonanes as Synthetic Intermediates. I. Improved Synthetic Methods for Bicyclo [3.3.1] nonan-3-one

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概要

• 論文の詳細を見る

• The syntheses of the title bicyclic ketone (IV) are described. The Michael-aldol condensation of ethyl acetoacetate (VI) with 2-cyclohexen-1-one (V) afforded a bicyclic β-keto ester, the ketonic cleavage of which gave 1-hydroxybicyclo [3.3.1] nonan-3-one (IX). Removal of the bridgehead hydroxyl in IX via the bromide (X) gave the desired ketone (IV). Another route to IV starting with bromination of adamantane followed by alkaline cleavage was established. Ozonolysis and subsequent ketalization converted 7-methylenebicyclo [3.3.1] nonan-3-one (XVII) into 7-ethylenedioxybicyclo [3.3.1] nonan-3-one (XIX), which was reduced to the desired ketone (IV) by means of the Huang-Minlon reduction. In addition, ozonolysis of 3-methylenebicyclo [3.3.1] nonane (XXII) gained by the Huang-Minlon reduction of XVII as a minor product was also found to give IV in good yield.

• 公益社団法人日本薬学会の論文
• 1978-01-25

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

• 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

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Muraoka O

  Shonai Regional Center For Plant Biotechnol. Yamagata

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