Enzymatic desymmetrization of a meso polyol corresponding to the C(19)-C(27) segment of rifamycin S

Authors
Chenevert, R Rose, YS
Citation
R. Chenevert et Ys. Rose, Enzymatic desymmetrization of a meso polyol corresponding to the C(19)-C(27) segment of rifamycin S, J ORG CHEM, 65(6), 2000, pp. 1707-1709
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
6
Year of publication
2000
Pages
1707 - 1709
Database
ISI
SICI code
0022-3263(20000324)65:6<1707:EDOAMP>2.0.ZU;2-B
Abstract
The stereoselective acylation of meso polyol 2 by vinyl acetate (solvent an d acyl donor) in the presence of porcine pancreas lipase gave the correspon ding monoester 5 in good yield (76%) and high enantiomeric purity (ee > 98% ). The enzymatic reaction was also highly regioselective for a primary alco hol end group, and the two unprotected secondary alcohols were not involved . Compound 5 corresponds to the C(19)-C(27) fragment of rifamycin S.