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■ 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

Abstract

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 (OBU^t)₃, respectively. The both alcohols afforded also corresponding spirobenzylisoquinolines with acids.