Stereochemically controlled synthesis of unsaturated acids by the coupled Baeyer–Villiger and Horner–Wittig reactions: synthesis of (Z)-oct-6-enoic acid

Abstract

The lithium derivative of Ph₂P(O)Et reacts with cyclohexene oxide to give largely one diastereoisomer of an alcohol. Oxidation to a ketone and then to a lactone followed by hydrolysis gives a Horner–Wittig intermediate and hence pure (Z)-oct-6-enoic acid. Complementary methods give (E)-oct-6-enoic acid.