Synthesis of Enantiomerically Pure (8<i>S</i>,9<i>S</i>,10<i>R</i>,6<i>Z</i>)‑Trihydroxyoctadec-6-enoic Acid

We have accomplished the asymmetric synthesis of (8<i>S</i>,9<i>S</i>,10<i>R</i>,6<i>Z</i>)-trihydroxyoctadec-6-enoic acid in optically pure form and determined the absolute configuration of the natural product on the basis of the stereodetermined chiral building block <b>7</b>, which was prepared by the catalytic enantioselective allylic oxidation of 4,5-epoxycyclohex-1-ene using an <i>S</i>-configured N,N-bidentate ligand–copper catalyst.