ENZYMATIC RESOLUTION OF 2-ACYL-3-HYDROXYMETHYL-4-BUTANOLIDE AND PREPARATION OF OPTICALLY-ACTIVE IM-2, THE AUTOREGULATOR FROM STREPTOMYCES SP FRI-5

Authors
MIZUNO K SAKUDA S NIHIRA T YAMADA Y
Citation
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
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
37
Year of publication
1994
Pages
10849 - 10858
Database
ISI
SICI code
0040-4020(1994)50:37<10849:ERO2AP>2.0.ZU;2-2
Abstract
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 ).