STEREOSELECTIVE SYNTHESIS OF 5 AND OR 6 MEMBERED RING HYDROXYLACTONESOBTAINED BY LEWIS-ACID MEDIATED REACTION OF GAMMA,DELTA-EPOXY-BETA-HYDROXYESTERS - ACCESS TO 5-METHYLATED 2-DEOXYSUGARS/

Authors
NACRO K BALTAS M ESCUDIER JM GORRICHON L
Citation
K. Nacro et al., STEREOSELECTIVE SYNTHESIS OF 5 AND OR 6 MEMBERED RING HYDROXYLACTONESOBTAINED BY LEWIS-ACID MEDIATED REACTION OF GAMMA,DELTA-EPOXY-BETA-HYDROXYESTERS - ACCESS TO 5-METHYLATED 2-DEOXYSUGARS/, Tetrahedron, 53(2), 1997, pp. 659-672
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
2
Year of publication
1997
Pages
659 - 672
Database
ISI
SICI code
0040-4020(1997)53:2<659:SSO5AO>2.0.ZU;2-Z
Abstract
A stereoselective route to six and/or five membered ring lactones from optically active gamma,delta-epoxy-beta-hydroxyesters obtained from n erol and geraniol has been developed. The intramolecular cyclization b y epoxide ring opening occurred via activation of 6-endo over the usua lly favoured 5-exo, and the application of this technology to the ster eocontrolled synthesis of 5-methylated 2-deoxysugars was achieved. Cop yright (C) 1996 Elsevier Science Ltd