Abstract
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.
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