Alkaloids of the Australian Rutaceae: Melicope fareana. II. Preliminary Examination of Melicopine, Melicopidine, and Melicopicine

Abstract

Four of the five oxygen atoms in the alkaloids melicopine, melicopidine, and melicopicine are present as alkoxyl groups, either methoxyl or methylenedioxy. In each alkaloid one of the methoxyl groups is remarkably sensitive to hydrolysis by acids. The resulting hydroxy compound is an alcohol, or more likely, an unreactive phenol. The methylenedioxy group in melicopine and melicopidine is attacked by alcoholic alkali and replaced by an hydroxyl and an alkoxyl group. The resulting phenols still contain the easily hydrolysed methoxyl group, the loss of which gives rise to a series of dihydroxy compounds. A number of acidic oxidation products is described.