Studies on the Syntheses of Heterocyclic Compounds. DCXLI A Convenient Synthesis of Hexadehydroyohimbine and a Total Synthesis of Yohimbine

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概要

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• A total synthesis of (±)-yohimbine (I) has been achieved from 1,2,3,4,5,6,7,12b-octahydroindolo[2,3-a]quinolizin-2-one (XXXIV) via 15,16-dehydroyohimbinone (XXXVII) and yohimbinone (XXXVIII). Moreover, hexadehydroyohimbine (XXIX) was synthesized from 2-bromo-5-methoxybenzaldehyde (VIII). α-Cyanophenylpropionic acid (X), prepared from VIII through the α-cyanocinnamic acid (IX), was cyclized to the indanone (XI), which was converted into 6-bromo-3-methoxy-2-methoxycarbonylphenylpropionic acid (XIV) via the corresponding dicarboxylic acid (XII) and diester (XIII). Debromination of XIV, followed by cyclization, gave the indanone (XXIII), which was transformed into the indan-1,2-dione (XXV) through the α-hydroxyimino ketone (XXIV). Pictet-Spengler reaction of XXV with tryptamine afforded the spirobenzyl-β-carboline (XXVI), whose photolysis yielded the decadehydroyohimbane (XXVII) and the decadehydroyohimban-21-one (XXVIII). Reduction of both products gave O-methylhexadehydroyohimbine (XXIX).

• 社団法人日本薬学会の論文
• 1975-11-25

著者

• 梶原 正宏

  Department of Medicinal Chemistry, Meiji College of Pharmacy

• 梶原 正宏

  Department Of Medicinal Chemistry Meiji College Of Pharmacy

• 亀谷 哲治

  Pharmaceutical Institute, Tohoku University School of Medicine

• 平井 美朗

  Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

• 福本 圭一郎

  東北大・薬

• 平井 美朗

  Pharmaceutical Institute, Tohoku University

• 福本 圭一郎

  Pharmaceutical Institute, Tohoku University

• 高橋 たみ子

  Pharmaceutical Institute Tohoku University

• 平井 美朗

  Pharmaceutical Institute Tohoku University

• 梶原 正宏

  Pharmaceutical Institute, Tohoku University

• 亀谷 哲治

  Pharmaceutical Institute Medical Faculty University Of Osaka

• 福本 圭一郎

  Pharmaceutical Institute Tohoku University School Of Medicine

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