Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XVI. On the Selectivity in the Ring Enlargement of the Bicyclo[3.3.1]nonan-2-one System

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概要

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• The stereochemistry in determining the migratory aptitude in the ring-expansion of bicyclo[3.3.1]nonane-2,6-dione 6-ethylene acetal (7) is discussed. The Tiffeneau-Demjanov ring-expansion of 6β-aminomethyl-6α-hydroxy-bicyclo[3.3.1]nonan-2-one 2-ethylene acetal (5,endo-alcohol) gave the homologous ketones (13 and 14) in the ratio of ca. 8 : 1,together with the endo-oxide (8). The reaction of the epimeric isomer, 6α-aminomethyl-6β-alcohol (6,exo-alcohol) gave the ketones 13 and 14 in the ratio of 2 : 1. The difference in the selectivity between two epimers was well interpreted in terms of least motion theory and the conformational stability of the intermediates. Hydrolysis of 13 and 14 led to two novel tricyclic systems, an isotwistane (15) and a protoadamantane (17), respectively.

• 社団法人日本薬学会の論文
• 1989-07-25

著者

• 村岡 修

  Faculty of Pharmaceutical Sciences, Kinki University

• 村岡 修

  Faculty Of Pharmaceutical Sciences Kinki University

• 峯松 敏江

  近畿大薬

• 百瀬 雄章

  Faculty of Pharmaceutical Sciences, Kinki University

• 百瀬 雄章

  富山医薬大・薬

• 峯松 敏江

  Faculty of Pharmaceutical Sciences, Kinki University

• 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

• 嶋田 徳彦

  Faculty of Pharmaceutical Sciences, Kinki University

• 辻本 知佳子

  Faculty of Pharmaceutical Sciences, Kinki University

• 峯松 敏江

  Faculty Of Pharmaceutical Sciences Kinki University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 辻本 知佳子

  Faculty Of Pharmaceutical Sciences Kinki University

• 嶋田 徳彦

  Faculty Of Pharmaceutical Sciences Kinki University

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