Enzymatic Resolutionof 2-Acyl-3-hydroxymethyl-4-butanolide and Preparation of Optically Active IM-2, the Autoregulator from Streptomyces sp. FRI-5

Article abstract of DOI:10.1016/S0040-4020(01)85697-0

Racemic 2-acyl-3-hydroxymethyl-4-butanolides were resolved through a lipase-catalyzed acylation with acetic anhydride.Optically active forms of 2-butyryl-3-hydroxymethyl-4-butanolide 14 obtained were used to prepare enantiomers of IM-2 10, the autoregulator from Streptomyces sp.FRI-5.The absolute configuration of IM-2 was deduced to be (2R,3R,6R).