Studies on the Syntheses of Heterocyclic Compounds. DXVI. Total Syntheses of the Aporphine, Morphinandienone, and Tetrahydrodibenzopyrrocoline Alkaloids by Benzyne Reaction

Abstract

Benzyne reaction of 1-(2-bromo-4, 5-methylenedioxybenzyl)-1, 2, 3, 4-tetrahydro-7-hydroxy-6-methoxy-2-methylisoquinoline (III) with sodium amide in liquid ammonia gave domesticine (II), amurine (X), and cryptowoline (XI) in one-step. The same reaction of the phenolic bromoisoquinoline (VI) gave thaliporphine (XV) O-methylflavinantine (XVI), and cryptaustoline (I).