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Communication | Special issue | Vol 28, No. 1, 1989, pp.63-65
Published online, 1st January, 1970
DOI: 10.3987/COM-88-S24
Enantioselective Synthesis of Naturally Occurring (—)-Tylophorine by Way of an Asymmetric Intramolecular Double Michael Reaction

Masataka Ihara, Yoshinobu Takino, Keiichiro Fukumoto,* and Tetsuji Kametani

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

Abstract

Treatment of the 8-phenylmenthyl α. β -unsaturated amide ester (3) with tert.-butyldimethylsilyl trifluoromethanesulfonate and triethylamine produced, with a complete diastereofacial selection, the indolizidines (4), which were converted into (-)-(R)-tylophorine (1).