TOTAL SYNTHESIS OF RACEMIC LYCORAMINE

The total synthesis of d,l-lycoramine (2), an Amaryllidaceae alkaloid, is described. The method utilizes the intermediacy of the biogenetically relevant hydrobenzazepines of type 22, readily available from cinnamonitrile precursors via a chemospecific cleavage of the more hindered C-6 methoxyl which ensures with concomitant 1,4-addition to the spirocyclic enone system and generates the complete galanthamine-like skeleton. The total synthesis of 2 proceeds in an overall 22% yield from 2,3-dimethoxycinnamonitrile.