Phenol oxidation and biosynthesis. Part XV. The biosynthesis of roemerine, anonaine, and mecambrine

Abstract

The relationship between the benzylisoquinoline alkaloid coclaurine and the aporphine alkaloid roemerine in Papaver dubium L. has been studied. Various congeners of coclaurine have also been utilised in the investigation of this biosynthesis. The corresponding biosynthesis of anonaine in Anona reticula L. has also been studied. The biosynthesis of mecambrine has been more briefly investigated. The relationship between mecambrine and roemerine has been demonstrated. The results as a whole provide good support for the previously enunciated hypothesis that aporphine alkaloids of the anonaine–roemerine type are derived from coclaurine-type precursors through phenol oxidation. Dienones of the crotonosine–mecambrine type are intermediates.