Studies on the Syntheses of Heterocyclic Compounds. DCLXXI. An Alternative Total Synthesis of Yohimbine

Abstract

Birch reduction of 16-carboxy-15, 16, 17, 18, 19, 20-hexadehydro-17-methoxyyohimbane (XII), followed by esterification with diazomethane, gave 15, 17, 18, 20-tetradehydro-17-meth-oxy-16-methoxycarbonylyohimbane (XIII), which was converted into 15, 16-dehydroyohimbinone (II). This was correlated with yohimbine (IV) by the present authors.