Phenolic Cyclization III. One Step Synthesis of cis- and trans-16-Hydroxy-15-methoxyerythrinanone by Phenolic Cyclization (Studies on the Syntheses of Heterocyclic Compounds. CCLXIV)

Abstract

cis-(IIa) and trans-16-Hydroxy-15-methoxyerythrinanone (IIb) were prepared by phenolic cyclization and the former (IIa) was transformed to corresponding cis-erythrinane (VII) by lithium aluminum hydride and to 15, 16-dimethoxyerythrinane (VI) via cis-15, 16 dimethoxyerythrinanone (Va). cis-(Va) and trans-15, 16-dimethoxyerythrinanone (Vb) were obtained from homoveratrylamine (VIII) and 2-carboxymethylcyclohexanone ethylene ketal (IX).