PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND MANNONOLACTAM FROM L-GULONOLACTONE. SYNTHESIS OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE.

Article abstract of DOI:10.1016/0040-4020(89)80059-6

An eight step synthesis of deoxymannojirimycin from L-gulonolactone in 25percent overall yield is reported; the key step is the formation of a δ-lactam by the reduction of a 5-azidolactone.The preparations of mannonolactam from L-gulonolactone and of L-deoxymannojirimycin and L-mannonolactam from D-gulonolactone are described.