Simple synthetic route to polyhydroxylated pyrrolidines and piperidines

Article abstract of DOI:10.1002/jhet.5570350334

A short and simple synthetic route to polyhydroxylated piperidines and pyrrolidines were described with D-glucurono-δ-lactone as chiral educt. Key reaction steps included selective cleavage of terminal isopropylidene group of compound 12 with Dowex 50W-X8 resin (H⁺ form), regioselective ring opening of epoxide 16 and intramolecular nucleophilic amination of compound 14 and 18.