A GENERAL AND STEREOSELECTIVE APPROACH TO NONACTATE ESTERS AND ISOMERS - A VERSATILE SYNTHESIS OF (-METHYL NONACTATE())

Authors
MANDVILLE G GIRARD C BLOCH R
Citation
G. Mandville et al., A GENERAL AND STEREOSELECTIVE APPROACH TO NONACTATE ESTERS AND ISOMERS - A VERSATILE SYNTHESIS OF (-METHYL NONACTATE()), Tetrahedron, 53(50), 1997, pp. 17079-17088
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
50
Year of publication
1997
Pages
17079 - 17088
Database
ISI
SICI code
0040-4020(1997)53:50<17079:AGASAT>2.0.ZU;2-4
Abstract
A total synthesis of (+)-methyl nonactate from a chiral synthon obtain ed by enantioselective enzymatic transesterification is described. Thi s new approach involves stereoselective reactions of aldolisation, red uction and intramolecular Michael addition and appears to be quite gen eral since it could be applied as well to the synthesis of both enanti omers of 2- or 8-epi nonactate esters or homologues. (C) 1997 Elsevier Science Ltd.