Lythraceous Alkaloids. II. The Structure of O-Methyllythranidine

Abstract

Permanganate oxidation of O-methyllythranidine gave the evidence for the presence of 2, 2'-disubstituted diphenyl group in the molecule. O, N-Dimethyllythranidine was subjected to repeated Hofmann degradations followed by hydrogenations to give des-N base V, which was oxidized to diketone VI. Subsequently, the presence of a piperidine ring in the alkaloid was proved by a series of reactions. Some reactions and nuclear magnetic resonance spectra investigations of the products led to a conclusion that O-methyllythranidine has structure A.