A Straightforward Synthesis of (+/-) 5-Amino-5,6-Dideoxyallose, of its Bisulfite β-Anomer, and of its 1-Deoxy Derivative.

Article abstract of DOI:10.1016/S0040-4039(00)79341-5

Diels-Alder cycloaddition of (E,E)-hexadienal dimethylacetal 3 with the benzyloxycarbonylnitroso dienophile 4, followed by catalytic osmylation, hydrogenolysis, and treatment with SO2, led stereospecifically to the sole β-anomer of allopiperidinose bisulfite derivative 7.Saponification of 7 and thence catalytic hydrogenation gave in high yield the 1-deoxyallopiperidine derivative 9.