LEWIS-ACID MEDIATED DIELS-ALDER REACTIONS OF 6-VINYLPURINES

Authors
OVERAS AT GUNDERSEN LL RISE F
Citation
At. Overas et al., LEWIS-ACID MEDIATED DIELS-ALDER REACTIONS OF 6-VINYLPURINES, Tetrahedron, 53(5), 1997, pp. 1777-1786
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
5
Year of publication
1997
Pages
1777 - 1786
Database
ISI
SICI code
0040-4020(1997)53:5<1777:LMDRO6>2.0.ZU;2-5
Abstract
6-Vinylpurines readily undergo Diels-Alder reactions with dienes. Both reactivity and endo selectivity are greatly improved when the cycload ditions are performed in the presence of zinc chloride. Lewis acid med iated Diels-Alder reaction of 6-vinylpurine riboside was employed as a key step in the synthesis of a nucleoside with structural resemblance to potent A(1) adenosine agonists. (C) 1997, Elsevier Science Ltd.