SYNTHESIS OF )-10-FLUORODECAN-9-OLIDE(FLUORO-PHORACANTHOLIDE-I) AND )-10-FLUORODECAN-9-OLIDE(FLUORO-PHORACANTHOLIDE-I) - FIRST LIPASE-CATALYZED ENANTIOSELECTIVE ESTERIFICATION OF BETA-FLUOROALCOHOLS

Authors
SATTLER A HAUFE G
Citation
A. Sattler et G. Haufe, SYNTHESIS OF )-10-FLUORODECAN-9-OLIDE(FLUORO-PHORACANTHOLIDE-I) AND )-10-FLUORODECAN-9-OLIDE(FLUORO-PHORACANTHOLIDE-I) - FIRST LIPASE-CATALYZED ENANTIOSELECTIVE ESTERIFICATION OF BETA-FLUOROALCOHOLS, Tetrahedron : asymmetry, 6(11), 1995, pp. 2841-2848
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
11
Year of publication
1995
Pages
2841 - 2848
Database
ISI
SICI code
0957-4166(1995)6:11<2841:SO)A)>2.0.ZU;2-B
Abstract
Synthesis of both enantiomers of fluoro-phoracantholide I, namely (9S) -10-fluorodecan-9-olide ((9S)-(-)-1) and (9R)-10-fluorodecan-9-olide ( 9R)-(+)-1, has been achieved through lipase-catalyzed enantioselective acetylation of methyl 10-fluoro-9-hydroxydecanoate (2a) with acetic a nhydride in the presence of Lipase Amano PS (Pseudomonas cepacia). The higher homologue, methyl 11-fluoro-10-hydroxyundecanoate (2b) has als o been resolved. These enzymatic resolutions by acetylation of omega-f luoro-(omega-1)-hydroxyalkanoic acid esters of long-chain fatty acids represent the first lipase-catalyzed enantioselective esterifications of beta-fluoroalcohols.