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Paper | Regular issue | Vol 45, No. 8, 1997, pp.1529-1536
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7830
Formation of 3-Iso-19-epicathenamine, Isolated as Its Cyano Adduct 21α-Cyano-3-isorauniticine

Mauri Lounasmaa* and Pirjo Hanhinen

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland

Abstract

Formation of 3-iso-19-epicathenamine (8), which is a plausible intermediate in the biogenetic formation of heteroyohimbine alkaloids 3-isorauniticine (11) and 3-iso-19-epiajmalicine (12), is described. Compound (8) was isolated as its cyano adduct, 21α-cyano-3-isorauniticine (17). The Brown and Leonards’ 21-cyano adduct, isolated after a biomimetic conversion process of a mixture of strictosidine (18) and vincoside (19), and for which the 21α-cyanoakuammigine structure (21) was claimed, is shown to be in reality identical with compound (17).