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Communication | Regular issue | Vol 14, No. 3, 1980, pp.303-310
Published online, 1st January, 1970
DOI: 10.3987/R-1980-03-0303
The Total Stereoselective Retro Mass Spectral Synthesis of (±)-Emetine

Tetsuji Kametani,* Samuel A. Surgenor, and Keiichiro Fukumoto

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


A new route to (±)-emetine (18) via the Michael addition product (4A) is described. Addition of 3,4-dihydro-6,7-dimethoxy-1-methylisoquinoline (3) to the α,β-unsaturated ester (2) afforded 2-(3’,4’-dihydro-6’,7’-dimethoxy-1’-isoquinolinylmethyl)-3-methoxycarbonyl-1,2,3,6,7,11b-hexahydro-9,10-dimethoxybenzo[a]quinolizin-4-one (4A) which was converted to (±)-emetine in 6 steps.