POLYHYDROXYLATED PYRROLIDINES FROM SUGAR LACTONES: SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-D-GLUCITOL FROM D-GALACTONOLACTONE AND SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-ALLITOL, 1,4-DIDEOXY-1,4-IMINO-D-RIBITOL, AND (2S,3R,4S)-3,4-DIHYDROXYPROLINE FROM D-GULONOLACTONE

Article abstract of DOI:10.1016/S0040-4020(01)81716-6

The use of readily available sugar lactones in the synthesis of polyhydroxylated pyrrolidines is illustrated by the preparation of the glucosidase inhibitor 1,4-dideoxy-1,4-imino-D-glucitol from D-galactonolactone and by the conversion of D-gulonolactone into 1,4-dideoxy-1,4-imino-D-allitol, 1,4-dideoxy-1,4-imino-D-ribitol, and (2S,3R,4S)-3,4-dihydroxyproline.