Alkenyl diols by E-Selective Horner-Wittig elimination: Formal synthesis of any isomer (RR, RS, SR or SS) bearing 1,5-related stereogenic centres across an E double bond

Article abstract of DOI:10.1016/S0040-4039(97)10859-0

Oxidation of diastereomerically pure diphenylphosphinoyl furans [e.g. 4-benzyloxy-2-diphenylphosphinoyl 1-(2'-furyl) octan-1-ol] with m-CPBA, followed by reduction with sodium borohydride, gives triols with four stereochemically controlled stereogenic centres. (E)-Selective Horner-Wittig elimination removes the middle two stereogenic centres to yield diols with 1,5-related stereogenic centres across a trans double bond.