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Report | Regular issue | Vol 19, No. 2, 1982, pp.313-318
Published online, 1st January, 1970
DOI: 10.3987/R-1982-02-0313
Conversion of Berberine into Benzindanoazepines via 8,14-Cycloberbines

Miyoji Hanaoka, Mitsuru Inoue, Kazuyoshi Nagami, Yasuji Shimada, and Shingo Yasuda

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

Acidic treatment of the 8,14-cycloberbine (2) effected regioselective C14-N bond cleavage to give the trans- and cis-benzindanoazepine (8a and 8b) as the kinetically and thermodynamically controlled product, respectively. Dehydration of their N-methyl derivatives (11a and 11b) afforded the unsaturated benzindanoazepine (13). Similarly the 11,12-oxygenated cycloberbine (19) was converted to the benzindanoazepines (20a, 20b, 21b, and 22). All these benzindanoazepines have been shown to be the key intermediates for the rhoeadine skeleton.