6-Deoxy-allo-nojirimycin in the racemic and D-series, 6-deoxy-D,L-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-D,L-allosamine via hetero-Diels-Alder cycloadditions

Article abstract of DOI:10.1016/S0040-4020(97)00897-1

Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cyclodducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6