Studies on the syntheses of heterocyclic compounds. 671. An alternative total synthesis of yohimbine.

Abstract

Birch reduction of 16-carboxy-15,16,17,18,19,20-hexadehydro-17-methoxyyohimbane, followed by esterification with diazomethane, gave 15,17,18,20-tetradehydro-17-methoxy-16-methoxycarbonylyohimbane, which was converted into 15,16-dehydroyohimbinone. This was correlated with yohimbine [Pausinystalia yohimba] [alkaloid] by the present study.