ISOLATION AND STRUCTURE OF A NEW ALKALOID: ASPIDOCARPINE

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Abstract
From the root bark of Aspidospermmegalocarpon Muell. Arg. a new alkaloid, aspidocarpine, has been isolated. It has the empirical formula C22H30O3N2 and contains an N-acetyl, one methoxyl group, and one active hydrogen. The alkaloid, a phenolic monoacidic tertiary base, has been shown by its properties, those of its derivatives, and the spectroscopic data, to contain an N-acetyl-6-methoxy-7-hydroxydihydroindole moiety. Oxidation of aspidocarpine with chromic acid gave rise to a product identical in all respects with apoaspidospermine obtained from the similar oxidation of aspidospermine. Since the structure of aspidospermine is known, the foregoing results establish the structure of the alkaloid aspidocarpine.