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Communication | Special issue | Vol 56, No. 1-2, 2002, pp.119-122
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)63
■ Preparation of Enantiomers of 17-Epoxy Eicosapentaenoic Acids and Their 18-Hydroxy Derivatives

Tadahiro Kato,* Toshio Nakai, Rumiko Ishikawa, and Yukiko Iio

*Department of Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan

Abstract

By the action of NBS in aq DME, dl-17-bromo-18-hydroxy EPA methyl ester 6 was prepared, which was effectively resolved by lipase PS and vinyl acetate in the presence of a thiacrown ether to give the resolved bromoacetate (7) and bromohydrin (8), each being transformed into the corresponding epoxide (3 and 4). The absolute configuration of 8 was established by the Kusumi-Moscher method. Both epoxides were treated with LDA to provide allyl alcohols (5a and b), accompanied with the formation of cyclopropyl derivatives (10a and b).