Asymmetric routes to azasugars from chiral bicyclic lactams. Synthesis of 1,4-dideoxy-1,4-imino-d-lyxitol; L-Deoxymannojirimycin; rhammo-1- Deoxynojirimycin and 1-deoxy-6-epicastanospermine

Article abstract of DOI:10.1016/S0040-4020(99)00454-8

Summary: By employing the appropriate chiral bicyclic lactams, the asymmetric total synthesis of four enantiopure azasugars mentioned in the title were successfully achieved. A series of diastereoselective oxidations (OsO₄/NMO) followed by diastereoselective reductions (BH₃, 9-BBN) gave good yields of the trisubstituted (16) and tetrasubstituted (2,3,4) pyrrolidine and piperidines respectively.