Chemical Transformation of Protoberberines. VII. Efficient Conversion of Protoberberines into Benzindenoazepines via 8,14-Cycloberbines

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概要

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• A simple and convenient transformation of berberine (1) into trans-, cis-, and unsaturated benzindenoazepines through regioselective C_<14>-N bond cleavage of 8,14-cycloberbines is described. Acidic treatment of the 8,14-cycloberbine (2) effected regioselective ring opening to afford the trans-and cis-benzindenoazepines (7a and 7b) as the kinetically and thermodynamically controlled products, respectively. Dehydration of their N-methyl derivatives (11a and 11b) gave the unsaturated benzindenoazepine (20), which was obtained more efficiently from the 8,14-cycloberbine (2) by treatment with p-toluenesulfonic acid in benzene followed by N-methylation. Similarly, the ring D-inverted 8,14-cycloberbine (23) was converted to the corresponding trans-, cis-, and unsaturated benzindenoazepines (24a, 24b, and 27,respectively).

• 社団法人日本薬学会の論文
• 1985-04-25

著者

• 井上 満

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 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

• KIM SINKYU

  College of Pharmacy, Kyung Hee University

• 嶋田 康治

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 嶋田 康治

  Faculty Of Pharmaceutical Sciences Kanazawa University

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