Galanthamine Chemistry. V. Formation of Hydroxyapogalanthamine from Galanthaminone and the Synthesis of its Trimethyl Ether.

Abstract

Treatment of galanthaminone with hydriodic acid gave hydroxyapogalanthamine, the structure of which has been elucidated by degradation to the known diphenic acid (IV). The trimethyl ether of hydroxyapogalanthamine has been synthesized by two methods, confirming the structure of this important transformation product of galanthaminone. Based on this and other chemical evidence it has been concluded that galanthamine is represented by formula (III).