Chemoenzymatic Synthesis of the Antifungal Compound(–)-Pestynol by a Convergent, Sonogashira Construction of the Central Yne-Diene

Abstract

A total synthesis of the fungal-derived natural prod-uct pestynol is reported via a convergent chemoenzymatic ap-proach from the readily available precursors geranyl bromide,ethyl acetoacetate, trimethylsilylacetylene, and bromobenzene. Synthetic (–)-pestynol proved to be identical in all respects to thenatural material, allowing confirmation of the structure includ-ing absolute stereochemistry.