Lewis-acid catalysed arylation of the hydroxyamino sugar moiety of the natural product SB-219383

The natural product SB-219383 1a contains an unique bicyclic hydroxyamino sugar moiety. Novel C-glycosidation reactions of this hydroxyamino sugar moiety are reported. The formation of a sugar nitrone intermediate is postulated which is subsequently trapped by electron-rich aromatic rings to yield C-aryl hydroxyamino sugars.