Studies in terpenoid biosynthesis. Part 38. The role of an 16β,17-epoxyaphidicolane in the minor biosynthetic pathway leading to aphidicolin

Abstract

The hydroxylation of [15-²H, 17-²H₃]aphidicolane-3α,16β,18-triol at C-17 in the biosynthesis of aphidicolin is shown to involve an isotope effect whilst there is no effect in the incorporation of [15-²H, 17-²H₂]aphidicol-16-ene-3α,18-diol suggesting that the transformation of the 16-ene involves epoxidation and hydrolysis rather than hydration and hydroxylation. Feeding experiments suggest that the 16β,17-epoxyaphidicolane-3α,18-diol is involved in this transformation.