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Communication | Special issue | Vol 7, No. 1, 1977, pp.143-147
Published online, 1st January, 1970
DOI: 10.3987/S-1977-01-0143
Synthesis of (±)-Emetine from Protoberberine Precursor via the α-Diketone Monothioletal Intermediate

Seiichi Takano,* Makoto Sasaki, Hideyuki Kanno, Kozo Shishido, and Kunio Ogasawara

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

Abstract

A synthesis of (±)-emetine (1) is accomplished using 2,3,11-trimethoxytetrahydroprotoberberine (3) as a starting material via the α-diketone monothioketal intermediate (8). Compound (3) was converted to the α-diketone monothioketal derivative (8) through a 4 step-sequence. The intermediate (8) upon treatment with potassium hydroxide, followed by desulfurization yielded the protoemetine derivative (11). (±)-Emetine (1) was obtained from 11 by a series of classical methods.