Chemical Transformation of Protoberberines. VIII. A Novel Synthesis of (±)-Fumaricine and a Formal Synthesis of (±)-Alpinigenine

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概要

• 論文の詳細を見る

• Berberine (1) was transformed stereoselectively into either the trans- or cis-hydroxyspiro-benzylisoquinoline (9 or 10) via the 8,14-cycloberbine (3). This method was applied to a first transformation of the protoberberine (22) into a spirobenzylisoquinoline alkaloid, (±)-fumaricine (6). Irradiation of the phenolbetaine (24) derived from the protoberberine (22) afforded its valence isomer, the 8,14-cycloberbine (25), treatment of which with ethyl chloroformate gave the spirobenzylisoquinoline (26). Hydrogenolysis of 26 followed by lithium aluminum hydride reduction provided (±)-fumaricine (6). Similarly, palmatine (31) was converted via the 8,14-cycloberbine (34) and the keto-urethane (35) into the trans-hydroxyspirobenzylisoquinoline (7), the key intermediate in a synthesis of (±)-alpinigenine (8), a rhoeadine alkaloid.

• 社団法人日本薬学会の論文
• 1985-06-25

著者

• 桜井 俊一郎

  北陸製薬株式会社中央研究所研究開発本部

• 花岡 美代次

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 花岡 美代次

  金沢大学薬学部

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 安田 信吾

  金沢大・薬

• 詠 和良

  Faculty of Pharmaceutical Sciecnes, Kanazawa University

• 詠 和良

  Faculty Of Pharmaceutical Sciecnes Kanazawa University

• 安田 信吾

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 平井 由利子

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 桜井 俊一郎

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 平井 由利子

  Faculty Of Pharmaceutical Sciences Kanazawa University

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