1,6-Dihydro-3 (2H)-pyridinones. III. A Formal Synthesis of (±)-Catharanthine

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概要

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• On treatment with ethyl vinyl ether containing mercuric acetate, the allylic alcohol (5) afforded the aldehyde (7), which was acetalized to 8. Hydroboration-oxidation of 8 was followed by pyridinium chlorochromate (PCC) oxidation to yield two isomeric ketones (11 and 12), of which the former was subjected to acidic hydrolysis to afford the 2-azabicyclo [2. 2. 2] octanone (3b) in excellent yield. On the other hand, the diketal (22) derived from 11 also gave the N-benzyloxycarbonyl analogue (3c) on acidic treatment. Ketalization of 3c and subsequent oxidation provided the ketone (27), which was transformed into the amide (29) via the amine (28). Cyclization of 29 furnished the pentacyclic product (30), which has already been converted into (±)-catharanthine (4) and (±)-velbanamine (31).

• 公益社団法人日本薬学会の論文
• 1982-11-25

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 八木 典幸

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 新 広昭

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 新 広昭

  Faculty Of Pharmaceutical Sciences Kanazawa University

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