Synthesis of Cularine Type Compounds (Studies on the Syntheses of Heterocyclic Compounds. CCXXXVI)

Abstract

1-(4-Hydroxy-3-methoxybenzyl)-6, 7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-8-ol (V) was oxidized with potassium ferricyanide to dienone (VI), which was subjected to dienone-phenol rearrangement with hydrochloric acid in acetic acid to give the cularine type compound (XXI). These reactions provide a possible model for biogenesis of cularine and related alkaloids. Moreover, this paper described the preparation of V.