SYNTHESIS OF CARBOHYDRATE MIMICS - ALPHA-1-C-SUBSTITUTED-DEOXYMANNOJIRIMYCINS

Authors
JOHNSON CR JOHNS BA
Citation
Cr. Johnson et Ba. Johns, SYNTHESIS OF CARBOHYDRATE MIMICS - ALPHA-1-C-SUBSTITUTED-DEOXYMANNOJIRIMYCINS, Tetrahedron letters, 38(46), 1997, pp. 7977-7980
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
46
Year of publication
1997
Pages
7977 - 7980
Database
ISI
SICI code
0040-4039(1997)38:46<7977:SOCM-A>2.0.ZU;2-0
Abstract
Methodology for the construction of diverse alpha-I-C-substituted-deox ymannojirimycin analogues is reported. The pseudoanomeric carbon-carbo n bond was formed using a Suzuki cross-coupling between vinyl bromide 5, derived biocatalytically from bromobenzene, and an aryl, alkyl, or carbohydrate boron coupling partner. Ozonolysis and stereoselective re duction followed by an intramolecular nucleophilic ring closing served to form the polyhydroxylated piperidine ring. (C) 1997 Elsevier Scien ce Ltd.