Synthesis of Polyhydroxy Azasugar via Chiral Epoxyaldehyde

Naturally occurring azasugar and homologous compounds have been the object of numerous synthetic efforts because these classes of compounds have interesting bioloical activities and the flexibility for the synthesis of chiral alkaloid comounds. As part of a program directed toward the preparation of glycosidase inhibitors, we prepared bicyclic perhydrooxazino- and oxazolopyridine from aminoalcohols and epoxyaldehyde as a common synthetic intermediate.