Chemical Transformation of Protoberberines. VI. Ring D Inversion of Protoberberine Alkaloids. Conversion of Berberine into Non-naturally Occurring 11,12-Oxygenated Protoberberines via Spirobenzylisoquinolines

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概要

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• Three methods were developed for the transformation of naturally occurring 9,10-oxygenated protoberberines into non-naturally occurring 11,12-oxygenated protoberberines through ring D inversion via spirobenzylisoquinolines. Berberine (14) was converted to the spirobenzylisoquinoline (18) through regioselective cleavage of the 8,14-cycloberbine (17). Alkaline hydrolysis of the oxazolidinone (20) derived from 18 efficiently afforded the 11,12-oxygenated protoberberine (23), which was also obtained from 8-methoxyberberinephenolbetaine (24) through treatment of the keto-hydroxy-spirobenzylisoquinoline (25) with alkali. The spirobenzylisoquinoline (26) derived from the 8,14-cycloberbine (16) was subjected to hydrogenolysis and subsequent hydrolysis to give the amino-ketone (28), photolysis of which furnished the 11,12-oxygenated protoberberine (29).

• 公益社団法人日本薬学会の論文
• 1984-11-25

著者

• 井上 満

  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

• 安田 信吾

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 高橋 みさを

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 高橋 みさを

  Faculty Of Pharmaceutical Sciences Kanazawa University

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