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■ Oxidative Transformation of Dihydrocoralyne to 6’-Acetylpapaveraldine

Jiro Imai and Yoshikazu Kondo*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Dihydrocoralyne III, obtained by partial reduction of coralynium salts in 86% yield, was autoxidized in solution at pH 8 to phenolbetaine IV in quantitative yield. Treatment of IV with m-chloroperbenzoic acid gave 6’-acetylpapaveraldine in 65% yield. Irradiation of III in the presence of air gave V in quantitative yield. The oxidative cleavage of IV was satis- factorily explained via the oxaziridine intermediate.