Enzyme catalysed lactonization of 3,5 dihydroxy esters: Enantioselective synthesis of naturally occurring 3-hydroxy-5-decanolide, (−)-massoialactone, and 3-hydroxy-5-icosanolide.

Abstract

Synthesis of optically active (+)-3-hydroxy-5-decanolide, (−)-massoialactone and of the recently isolated 3-hydroxy-5-icosanolide was achieved by enzyme-catalysed lactonization of racemic 3,5 dihydroxy esters with PPL in dry Et 2O. Ees vary from 86% up to >98%.