Cr. Johnson et Ba. Johns, SYNTHESIS OF CARBOHYDRATE MIMICS - ALPHA-1-C-SUBSTITUTED-DEOXYMANNOJIRIMYCINS, Tetrahedron letters, 38(46), 1997, pp. 7977-7980
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.