Novel Biogenetic Pathways from (+)-Reticuline. Three Dimeric Alkaloids: (+)-Vanuatine, (+)-Vateamine, and (+)-Malekulatine

Article abstract of DOI:10.1021/jo00170a016

The bark of Hernandia peltata Meissner (Hernandiaceae), gathered in the Republic of Vanuatu (New Hebrides), has yielded the bis(benzylisoquinolines) (+)-vanuatine (5), (+)-vateamine (6), and (+)-malekulatine (7).These are the first-known dimers of (+)-reticuline (2).Compounds 5 and 6 are products of tail-to-tail oxidative coupling, whereas 7 involves head-to-tail coupling.