Studies toward Total Synthesis of Non-aromatic Erythring Alkaloids. (6). Synthesis of 8-OXO-γ-erythroidine and 8-Oxo-cycloerythroidine, Isomers of the Natural Alkaloids.

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概要

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• A study directed to the total synthesis of β-erythroidine 1,a non-aromatic Erythrina alkaloid, was conducted based on a strategy involving construction of D-furanoerythrinan via Diels-Alder reaction of furodioxopyrroline and the conversion of the resulting furan to the δ-lactone via oxidative fission of the furan ring followed by one-carbon homologation. Oxidation of the furanoerythrinan 17 with N-bromoacetamide followed by treatment with Nafion-H gave the enol γ-lactone 27. Alkaline hydrolysis of 27 followed by methylation with diazomethane gave the keto-ester 31. Alkylation of 31a with dimethylsulfoxonium methylide gave 8-oxo-γ-erythrodine (5). One-carbon homologation of 31a by Yamakawa's method using chloromethyl phenyl sulfoxide resulted in the formation of 8-ozocycloerythroidine (6). Compounds 5 and 6 are structural isomers of natural 8-oxo-β-erthroidine (2).

• 社団法人日本薬学会の論文
• 1992-12-25

著者

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 礒部 公明

  昭和薬大

• 礒部 公明

  Showa College of Pharmaceutical Sciences

• 細井 深造

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 細井 深造

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 佐野 武弘

  Showa College of Pharmaceutical Sciences.

• 安藤 弘美

  Showa College Of Pharmaceutical Sciences

• 山本 隆三

  Showa College Of Pharmaceutical Sciences

• 津田 喜典

  金沢大薬

• 戸田 潤

  Showa College of Pharmaceutical Sciences

• 正田 基

  Showa College of Pharmaceutical Sciences

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 佐野 武弘

  Showa College Of Pharmaceutical Sciences

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