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A stereoselective synthesis of 1-deoxynojirimycin, D-glucono-δ-lactam and D-altrono-δ-lactam were accomplished from a common chiral intermediate derived from D-mannitol. The key transformations in the synthesis include Miyashita C-2 selective endo-mode azide opening of epoxy alcohol and Sharpless asymmetric dihydroxylation.

Stereoselective synthesis of 1-deoxynojirimycin, D-glucono-δ-lactam and D-altrono-δ-lactam from a common chiral intermediate derived from D-mannitol