Studies on the Syntheses of Heterocyclic Compounds. CDLXXXII. Total Photolytic Synthesis of (±)-Epicrinine

Abstract

Photolytic intramolecular cyclization of N-(4-hydroxyphenethyl)-2-bromo-4, 5-methylenedioxybenzylamine (Va) gave (±)-oxocrinine (VI). Meerwein-Ponndorf reaction of VI resulted in the exclusive formation of (±)-epicrinine (I), similar to the reduction of VI, employing lithium aluminum hydride. The same reaction of N-(2-hydroxy-3-methoxyphenethyl)-2-bromo-4, 5-methylenedioxybenzylamine (Vb) was also examined.