Synthesis of four stereoisomers of the higher dipteran juvenile hormone III bisepoxide

Article abstract of DOI:10.1016/S0040-4039(00)74741-1

The 6S,7S,10R-, 6S,7S,10S-, 6R,7R,10S-, and 6R,7R,10R-stereoisomers of the juvenile hormone III bisepoxide from higher Dipteran insects have been synthesised in high stereoisomeric purity. The route involves Sharpless epoxidation of geraniol to enantiomeric epoxyalcohols, which are each elaborated via separable diastereomeric bromohydrins.