The alkaloids of Elmerrillia papuana (Magnoliaceae) : Structure and synthesis of elmerrillicine

Abstract

From the bark of Elmerrillia papuana (Schltr.) Dandy (Magnoliaceae) were isolated the known alkaloids liriodenine, norushinsunine (as its diacetyl derivative) and N-methylushinsunine iodide, together with a new alkaloid, elmerrillicine (as its monoacetyl and diacetyl derivatives). By spectroscopic methods elmerrillicine was deduced to be 3-methoxy-l,2-methylenedioxy-6-demethylaporphin-11-ol, This structure was confirmed by a synthesis by the standard route involving a Pschorr reaction and by a photochemical synthesis in which a dehydroaporphine was an intermediate.