Asymmetric routes to azasugars from chiral bicyclic lactams. Synthesis of 1,4-dideoxy-1,4-imino-D-lyxitol; L-deoxymannojirimycin; rhammo-1-deoxynojirimycin and 1-deoxy-6-epicastanospermine.

Authors
Meyers, AI Andres, CJ Resek, JE Woodall, CC McLaughlin, MA Lee, PH Price, DA
Citation
Ai. Meyers et al., Asymmetric routes to azasugars from chiral bicyclic lactams. Synthesis of 1,4-dideoxy-1,4-imino-D-lyxitol; L-deoxymannojirimycin; rhammo-1-deoxynojirimycin and 1-deoxy-6-epicastanospermine., TETRAHEDRON, 55(29), 1999, pp. 8931-8952
Citations number
52
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
29
Year of publication
1999
Pages
8931 - 8952
Database
ISI
SICI code
0040-4020(19990716)55:29<8931:ARTAFC>2.0.ZU;2-E
Abstract
By employing the appropriate chiral bicyclic lactams, the asymmetric total synthesis of four enantiopure azasugars mentioned in the title were success fully achieved. A series of diastereoselective oxidations (OsO4/NMO) follow ed by diastereoselective reductions (BH3, 9-BBN) gave good yields of the tr isubstituted (16) and tetrasubstituted (2,3,4) pyrrolidine and piperidines respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.