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Communication | Special issue | Vol 46, No. 1, 1997, pp.137-140
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S48
Enantiocontrolled Synthesis of (11S,12S,13S)-(9Z,15Z)- and (11R,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxy Octadecadienoic Acids by Means of the Sharpless Asymmetric Epoxidation of the Unsymmetrical Divinylcarbinol

Toshio Honda,* Mai Ohta, and Hirotake Mizutani

*Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

(11S,12S,13S)-(9Z,15Z)- and (11R,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxy octadecadienoic acids, self defensive substances against the rice blast disease, were synthesized enantioselectively by employing the Sharpless asymmetric epoxidation reaction of the unsymmetrical divinylcarbinol, as a key step.