Template-directed intramolecular C-glycosidation. Formation of tetrahydrofurans and application to the synthesis of a higher-order sugar

Authors
Craig, D Pennington, MW Warner, P
Citation
D. Craig et al., Template-directed intramolecular C-glycosidation. Formation of tetrahydrofurans and application to the synthesis of a higher-order sugar, TETRAHEDRON, 55(47), 1999, pp. 13495-13512
Citations number
34
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
47
Year of publication
1999
Pages
13495 - 13512
Database
ISI
SICI code
0040-4020(19991119)55:47<13495:TICFOT>2.0.ZU;2-H
Abstract
Cation-mediated cyclisation reactions of silyl enol ether-containing :thiog lycosides give bicyclic ketotetrahydrofurans. Cyclisation of an analogous 3 -phenyl-2-propenyl ether-containing substrate gives an intermediate in the total synthesis of the higher-order sugar 2,3-didebxy-D-manno-2-octulopyran osonic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.