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Paper | Regular issue | Vol 87, No. 6, 2013, pp.1269-1278
Published online, 10th May, 2013
DOI: 10.3987/COM-13-12714
Development of a Novel Method for Warfarin Synthesis via Lipase-Catalyzed Steroselective Michael Reaction

Kaoru Sano, Shun-ichi Saito, Yoshihiko Hirose, Yoshihito Kohari, Hiroto Nakano, Chigusa Seki, Michio Tokiwa, Mitsuhiro Takeshita, and Koji Uwai*

*Department of Applied Sciences, Graduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto, Muroran, Hokkaido 050-8585, Japan

Abstract

Steroselective synthesis of warfarin by promiscuous lipase-catalyzed Michael addition of 4-hydroxycoumarin and benzylideneacetone has been developed. The best result was obtained using lipase AS as a catalyst in anhydrous dimethylsulfoxide (DMSO) with 1:3 molar ratio of 4-hydroxycoumarin to benzylideneacetone at 20ºC for 7 d. The yield and enantiomeric excess were 85% and 45%ee (R-form), respectively.