Synthesis of carbohydrate mimics: α-1-C-substituted-deoxymannojirimycins

Article abstract of DOI:10.1016/S0040-4039(97)10144-7

Methodology for the construction of diverse α-1-C-substituted-deoxymannojirimycin analogues is reported. The pseudoanomeric carbon-carbon bond was found 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 reduction followed by an intramolecular nucleophilic ring closing served to form the polyhydroxylated piperidine ring.