ADDITION OF ALLYLSTANNANES TO GLYCAL EPOXIDES - A DIASTEREOSELECTIVE APPROACH TO BETA-C-GLYCOSIDATION

Authors
EVANS DA TROTTER BW COTE B
Citation
Da. Evans et al., ADDITION OF ALLYLSTANNANES TO GLYCAL EPOXIDES - A DIASTEREOSELECTIVE APPROACH TO BETA-C-GLYCOSIDATION, Tetrahedron letters, 39(13), 1998, pp. 1709-1712
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
13
Year of publication
1998
Pages
1709 - 1712
Database
ISI
SICI code
0040-4039(1998)39:13<1709:AOATGE>2.0.ZU;2-H
Abstract
A new method for the synthesis of beta-C-allyl glycosides has been dev eloped for use in the synthesis of the spongipyran macrolides. Functio nalized dihydropyrans are transformed to cia tetrahydropyrans via a tw o step process: i) epoxidation using dimethyldioxirane and ii) Lewis a cid mediated epoxide opening with allylstannanes as nucleophiles. This protocol, which can be successfully applied to complex systems, augme nts the limited body of methodology available for the preparation of b eta-configured C-glycosides. (C) 1998 Elsevier Science Ltd. All rights reserved.