Transformation Products of Salutarine and Their ¹³C-Nuclear Magnetic Resonance Spectra

Abstract

Salutarine, the principal alkaloid of Croton salutaris CASAR has been treated with phenyllithium and methyllithium to yield the corresponding salutarinols. treatment of 7-phenylsalutarinol (not isolated) with acid produced the racemic form of 7-phenylthebaine. The mixture of epimeric 7-methylsalutarinols yielded mainly the dehydration product, the 7-methylene derivative of salutarine. A comparison of the ¹³C-nuclear magnetic resonance spectra of these and other derivatives of salutarine permitted a complete assignment of the chemical shifts.