Alkaloids of the Australian Rutaceae: Melicope fareana. III. Oxidative Demethylation of Melicopicine

Abstract

Melicopicine and normelicopicine undergo oxidative demethylation with nitric acid giving rise to isomeric dimethoxyquinones. These are further demethylated by alkali to the same hydroxymethoxyquinone which is converted by hydrobromic acid to a dihydroxyquinone. All the quinones can be reductively methylated back to melicopicine.