A NOVEL AND FLEXIBLE SYNTHESIS OF PYRANOSE SPIROACETAL DERIVATIVES

Authors
VANHOOFT PAV LEEUWENBURGH MA OVERKLEEFT HS VANDERMAREL GA VANBOECKEL CAA VANBOOM JH
Citation
Pav. Vanhooft et al., A NOVEL AND FLEXIBLE SYNTHESIS OF PYRANOSE SPIROACETAL DERIVATIVES, Tetrahedron letters, 39(33), 1998, pp. 6061-6064
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
33
Year of publication
1998
Pages
6061 - 6064
Database
ISI
SICI code
0040-4039(1998)39:33<6061:ANAFSO>2.0.ZU;2-0
Abstract
A three-step approach to chiral pyranose [5,4], [5,5], [5,6] and [5,7] unsaturated spiroacetal derivatives from perbenzylated glucopyranolac tone 1 is presented. The strategy involves Grignard addition of vinyl or allyl magnesium bromide to 1 to give 2 and 12, respectively, K-10 m ediated glucosidation of different terminal alkenols with 2 and 12 fol lowed by ring-closing metathesis. (C) 1998 Elsevier Science Ltd. All r ights reserved.