POTENT GLYCOSIDASE INHIBITORS VIA HETERO-DIELS-ALDER REACTIONS - ASYMMETRIC-SYNTHESIS OF 5-METHYL-TRIHYDROXYPYRROLIDINES

Authors
DEFOIN A SIFFERLEN T STREITH J DOSBAA I FOGLIETTI MJ
Citation
A. Defoin et al., POTENT GLYCOSIDASE INHIBITORS VIA HETERO-DIELS-ALDER REACTIONS - ASYMMETRIC-SYNTHESIS OF 5-METHYL-TRIHYDROXYPYRROLIDINES, Tetrahedron : asymmetry, 8(3), 1997, pp. 363-366
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
3
Year of publication
1997
Pages
363 - 366
Database
ISI
SICI code
0957-4166(1997)8:3<363:PGIVHR>2.0.ZU;2-C
Abstract
Some straightforward chemical transformations of oxazine diol 4, which was obtained from sorbaldehyde 2 by an asymmetric hetero Diels-Alder reaction followed by osmylation, led to the protected dihydroxypyrroli dine-aldehyde 8a and, after basic epimerisation, to 8b. Reduction of t he aldehyde moiety and deprotection gave the potent glycosidase inhibi tors 2,5,6-trideoxy-2,5-imino-D-altritol and D-allitol 9a and 9b. (C) 1997 Elsevier Science Ltd. All rights reserved.