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Communication | Regular issue | Vol 19, No. 12, 1982, pp.2263-2268
Published online, 1st January, 1970
DOI: 10.3987/R-1982-12-2263
Simple Conversion of 8-Alkyl-8,14-cycloberbines to Spirobenzylisoquinolines by Regioselective C-N Bond Cleavage

Miyoji Hanaoka, Shun-ichiro Sakurai, Yuko Sato, and Chisato Mukai

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


On acidic treatment the 8-alkyl-8,14-cycloberbines (10) were converted easily to the spirobenzylisoquinolines (11, 12, or 13) in good yields. Reduction of 10 gave stereoselectively the diastereoisomeric alcohols (14 or 15) depending on the reagents, NaBH4 or LiA1H (OBUt)3, respectively. The both alcohols afforded also corresponding spirobenzylisoquinolines with acids.