D. Chemin et G. Linstrumelle, AN EFFICIENT STEREOCONTROLLED SYNTHESIS OF METHYL (9Z,11E,13S)-13-HYDROXYOCTADECA-9,11-DIENOATE (METHYL CORIOLATE), Synthesis, (4), 1993, pp. 377-379
An efficient synthesis of methyl (13S)-coriolate (S)-1b is accomplishe
d by the palladium-catalyzed coupling of (1E,3S)-1-iodooct-1-en-3-ol [
(S)-3] with methyl dec-9-ynoate (4) followed by selective reduction of
the enyne (S)-2.