Studies on the Alkaloids of Menispermaceuos Plants. (Macao Tomita) LXXXIX

On the Structure of Biscoclaurine Alkaloids. (7). Cleavage of O-Methyloxyacanthine by Metallic Sodium in Liquid Ammonia. (1)

Abstract

When O-methyloxyacanthine is reacted by metallic sodium in liquid ammonia, d-1-(4'-hydroxybenzyl)-6, 7-dimethoxy-N-methyl-1, 2, 3, 4-tetrahydroisoquinoline (d-armepav-ine) (IV) is obtained in an yield of about 50% of the bisected phenolic base. As a result of this, it has been recognized that the cleavage proceeds under the type shown in formula (III), and has proved directly that the structure of oxyacanthine is as represented by formula (I).