Abstract The syntheses of the four imidazolo-piperidino-pentoses 3− 6, which belong to the D-series, and of their L-enantiomers, ent-3 to ent-6, are reported. Ascorbic acid and isoascorbic acid were converted over several steps into the L-threo/L-erythro-and the D- erythro/D-threo-configured aldotetroses, respectively, which are the key building blocks for the eight target imidazolo-pentoses cited above. Nucleophilic addition of a metallated ...