Synthesis of four stereoisomers of 5-amino-2,5-dideoxy-heptono-1,5-lactams

Article abstract of DOI:10.1016/S0040-4020(97)00738-2

The reaction of 2-trimethylsilyloxyfuran with a glyceraldehyde derived nitrone is examined under different reaction conditions. The four intermediates, tetrahydrofuro[2,3-d]isoxazol-5(2H)ones, were separated by combined chromatographic-crystallisation techniques. The synthetic versatility of tetrahydrofuro[2,3-d]isoxazol-5(2H)ones is demonstrated by a direct high yielding conversion into 5-amino-2,5-dideoxy-heptono-1,5-lactoms upon simple hydrogenolysis in the presence of Pearlman catalyst.