The stereoselective synthesis of (–)-(8R)-methylcanadine via selective monocomplexation of canadine to chromium tricarbonyl

Abstract

Regiospecific complexation of the dimethoxy arene ring of (–)-canadine to chromium tricarbonyl, protection of the C-11 position, followed by stereoselective substitution at C-8 effects, after deprotection and decomplexation, a stereoselective synthesis of (–)-(8R)-methylcanadine; a comparison is made with a racemic sample synthesised by an alternative route.