Bisbenzylisoquinoline Alkaloids and Related Compounds. XI. Total Synthesis of Stereoisomeric Mixture of Magnoline

Abstract

The diamide (IX) was prepared by Schotten-Baumann reaction of 2-(3-methoxy-4-hydroxyphenyl) ethylamine with the diacid chloride (V), followed by ethoxycarbonylation. Cyclization gave the bisdihydroisoquinoline (XI), the dimethiodide of which, on reduction, gave a stereoisomeric mixture of magnoline or berbamunine (I).