Stereochemical Studies. XLIX. A Biogenetic-type Total Synthesis of Natural (+)-Maritidine from L-Tyrosine using highly Specific Asymmetric Cyclization

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概要

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• A first biogenetic-type asymmetric synthesis of natural (+)-maritidine from L-tyrosine is described. Phenolic oxidative coupline of monophenol (10b) with thallium (III) trifluoroacetate afforded the corresponding spiro dienone (11b) in 66.5% yield. Asymmetric cyclization of dienone (14) was found to occur highly selectively to give one diastereomer (15) preferentially. Removal of the carboxamide group in 15 was effected by reductive decyanization of the intermediate amino nitrile (18) by sodium in liquid ammonia to (+)-epimaritidine (19), which was epimerized to the objective (+)-maritidine by the known method.

• 公益社団法人日本薬学会の論文
• 1977-10-25

著者

• 古賀 憲司

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• Koga Kenjiro

  Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hokuriku University

• 富岡 清

  Faculty of Pharmaceutical Sciences, University of Tokyo

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