Cularine and Related Compounds. XIV. : Optical Resolution of (±)-Cularimine and Synthesis of Related Compounds of Cularimine : Studies on the Syntheses of Heterocyclic Compounds. CLXVI.

Abstract

Cularimine (I) has been synthesized from a dicarboxylic acid (II) through four steps and examinations were made on an improved method for the synthesis of II. It was thereby found that reduction of the dialdehyde compound (III) with sodium borohydride to the alcohol (IV), its conversion to the nitrile (VI) through V, and hydrolysis of VI gave II in a good yield. This increased the total yield of I over that already reported. Optical resolution of (±)-cularimine using di-p-toluoyl tartaric acid was found to give the two optically active cularimines.