HALOCYCLIZATION AND PALLADIUM(II)-CATALYZED AMIDOCARBONYLATION OF UNSATURATED AMINOPOLYOLS - SYNTHESIS OF 1,4-IMINOGLYCITOLS AS POTENTIAL GLYCOSIDASE INHIBITORS

Authors
HUMMER W DUBOIS E GRACZA T JAGER V
Citation
W. Hummer et al., HALOCYCLIZATION AND PALLADIUM(II)-CATALYZED AMIDOCARBONYLATION OF UNSATURATED AMINOPOLYOLS - SYNTHESIS OF 1,4-IMINOGLYCITOLS AS POTENTIAL GLYCOSIDASE INHIBITORS, Synthesis, (6), 1997, pp. 634
Citations number
92
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
6
Year of publication
1997
Database
ISI
SICI code
0039-7881(1997):6<634:HAPAOU>2.0.ZU;2-F
Abstract
Syntheses of optically active 2,5-anhydro-1,4-dideoxy-1,4-imino-D-lyxi tol (6), 1,4,5-trideoxy-1,4-imino-D-lyxo-hexitol (14). and its N-methy l derivative 15 from achiral divinylcarbinol, via the amino-pentenedio l 1, are described using halogen-promoted cyclization and Pd(II)-catal yzed amidocarbonylation as key steps. 2,5,6-Trideoxy-2,5-imino-L-ido-h eptitol (23), a diastereomeric homologue of the naturally occurring py rrolidine DMDP G, is prepared from D-glucosamine hydrochloride in 7 st eps in 19% overall yield. The new compounds 6, 14, 15, and 23 show wea k glycosidase inhibition in two cases.