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Communication | Regular issue | Vol 4, No. 1, 1976, pp.29-33
Published online, 1st January, 1970
DOI: 10.3987/R-1976-01-0029
An Alternative Synthesis of (±)-Yohimbine

Tetsuji Kametani,* Yoshiro Hirai, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Birch reduction of 16-carboxyl-l5,16,17,18,19, 20-hexadehydro-17-methoxyyohimbane (8), followed by esterification gave 15,17,18,20-tetradehydro-17-methoxy- 16-methoxycarbonylyohimbane (10), which was treated with oxalic acid and then hydrochloric acid to afford 15,16-dehydroyohimbinone (2) that had been already correlated with (±)-yohimbine (4).