Studies on the Syntheses of Heterocyclic Compounds. CDLXXXVIII. An Alternative Synthesis of"Isocularine"by an Intramolecular Ullmann Reaction

Abstract

5, 5a, 6, 7, 8-Pentahydro-1-hydroxy-2, 11-dimethoxybenzo [b] oxepino [7, 6, 5-ij] isoquinoline (III) was synthesized by an intramolecular Ullmann reaction of 1-(3-benzyloxy-2-bromo-4-methoxybenzyl)-5-bromo-1, 2, 3, 4-tetrahydro-8-hydroxy-7-methoxy-2-methylisoquinoline (X), followed by hydrogenolysis of the product (XI), and also by reduction of N-ethoxycarbonyl analogue (XV) derived from Ullmann reaction product (XIV) of the phenolic bromoisoquinoline (XIII).