Enantiocontrolled synthesis of naturally occurring octadecadienoic acid derivatives, self-defensive substances against rice blast disease, by means of the Sharpless asymmetric epoxidation of unsymmetrical divinylmethanol1

Abstract

(11S,12S,13S)-(9Z,15Z)- and (11R,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadecadienoic acids and (11R,12S,13S)-(9Z,15Z)-11,12,13-trihydroxyoctadecadienoic acid, self-defensive substances against the rice blast disease, were synthesised enantioselectively by employing the Sharpless asymmetric epoxidation reaction of the unsymmetrical divinylmethanol, as a key step.