Alkaloids of Cryptocarya phyllostemon

Abstract

The known alkaloids (-)-antofine (1), dehydroantofine (5),(-)-cryptowoline (6), (4- cryptowolidine (7), and (-)-cryptowolinol (8), were isolated from the New Caledonian lauraceous plant Cryptocarya phyllosternon, together with five new bases: two secophenanthro-indolizidines, (-)-phyllostemine (2) and (-)-phyllosteminine (3), one pyrrolidinylacetophenone, (-)-phyllostone (4), and two quaternary tetrahydrobenzylisoquinolines, (+)-phyllocryptine (9) and (+)-phyllocryptonine (10). Chemical and spectroscopic methods were used for identification and structural investigation. A synthesis of phyllocryptonine has permitted its stereostructure to be determined.