Efficient synthesis of carbohydrate-containing carbocyclic compounds basedon palladium-catalyzed vinylation of sugars and subsequent Diels-Alder reaction

Authors
Hayashi, M Tsukada, K Kawabata, H Lamberth, C
Citation
M. Hayashi et al., Efficient synthesis of carbohydrate-containing carbocyclic compounds basedon palladium-catalyzed vinylation of sugars and subsequent Diels-Alder reaction, TETRAHEDRON, 55(42), 1999, pp. 12287-12294
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
42
Year of publication
1999
Pages
12287 - 12294
Database
ISI
SICI code
0040-4020(19991015)55:42<12287:ESOCCC>2.0.ZU;2-4
Abstract
In the presence of catalytic amount of Pd(dba)(2) and P(o-tol)(3), the reac tion of 3,4,6-tri-O-acetyl-2-bromo-D-glucal with ethylene proceeded smoothl y to afford the conjugated dieno-pyranoside in high yield. The Diels-Alder reaction of this carbohydrate-derived diene with some dienophiles construct ed chiral carbocyclic system. (C) 1999 Elsevier Science Ltd. All rights res erved.