K. Mizuno et al., ENZYMATIC RESOLUTION OF 2-ACYL-3-HYDROXYMETHYL-4-BUTANOLIDE AND PREPARATION OF OPTICALLY-ACTIVE IM-2, THE AUTOREGULATOR FROM STREPTOMYCES SP FRI-5, Tetrahedron, 50(37), 1994, pp. 10849-10858
Racemic 2-acyl-3-hydroxymethyl-4-butanolides were resolved through a l
ipase-catalyzed acylation with acetic anhydride. Optically active form
s of 2-butyryl-3-hydroxymethyl-4-butanolide 14 obtained were used to p
repare 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
).