Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems

Article abstract of DOI:10.1016/S0040-4020(01)90234-0

Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidene-D-glycero-L-altro-octonate (23), could be converted in two steps into a β-lactam.