Diastereoselective synthesis of the tetrahydropyranoid core of the polyketide herbicide herboxidiene and model studies pertaining to attachment of the side-chain

Abstract

A diastereoselective synthesis of compound 2, which embodies the tetrahydropyranyl core of the polyketide herbicide herboxidiene (1), has been developed using asymmetric epoxidation of nerol as the initial step. Ketone 2 has been elaborated to phosphine oxide 24 which engages in a Horner–Wittig reaction with nonanal to give the E,E-diene 27, an analogue of herboxidiene. However, unlike compound 1, congeners 2 and 27 are not phytotoxic.