Chemistry of the Podocarpaceae. LII. Demethylation involving partial inversion of cofiguration at two remote centres

Abstract

Treatment of optically pure (+)-12-methoxypodocarpa-8,11,13-triene (2) with HI/HBr/HOAc and a trace of H₃PO₂ gives, as the major product, a non-racemic mixture of (+)-podocarpa-8,11,13-trien-12-ol (3) and its enantiomer (14).