A new and highly stereoselective synthesis of polyhydroxyindolizidines from 4-octulose derivatives

Article abstract of DOI:10.1016/S0957-4166(98)00064-0

(1S,2S,6R,7R,8R,8aR)-1,2,6,7,8-Pentahydroxyindolizidine 12 and (1R,6R,7R,8R,8aR)-1,6,7,8-tetrahydroxy-indolizidine (1,6- diepicastanospermine, 24) have been stereoselectively synthesized from the important key intermediates 1,4-dideoxy-1,4-imino-D-erythro-L-altro-octitol 7 and 1,2,4-trideoxy-1,4-imino-D-glycero-D-talo-octitol 20 in three steps. Compounds 7 and 20 were readily obtained from 2,3:4,5:6,7-tri-O- isopropylidene-β-D-glycero-D-galacto-oct-4-ulo-4,8-pyranose 1 and 2-deoxy- 4,5:6,7-di-O-isopropylidene-β-D-manno-oct-4-ulo-4,8 pyranose 13 in four steps, respectively.