New reactions of phthalidoisoquinoline alkaloids. Alkoxy exchange reactions and isomerisations of α- and β-narcotine

Article abstract of DOI:10.1002/ardp.19783110804

Substitution of the 7-methoxy group in α- and β-narcotine by other alkoxy groups occurs in an anhydrous ROH/RONa system. It is accompanied by isomerization in position 3 with preference for the α-configuration (5R, 3S). In an alkaline aqueous system (ROH/KOH or 1N KOH only isomerization in position 3 with preference for the β-configuration (5R, 3R) was observed. Some of the new 7-alkoxynarcotines were evaluated for their antitussive activity.