Preparation of enantiomerically pure 2-(1′-aminomethyl)furan derivatives and synthesis of an unnatural polyhydroxylated piperidine

Zinc-mediated propargylation of α-acylaminoaldehydes, and subsequent oxidative isomerization followed by Ag(I)-catalyzed cycloisomerization conveniently provides a new enantioselective route to the corresponding 2-aminoalkylfurans. One of these furans was successfully converted into an unnatural polyhydroxylated piperidine that efficiently incorporated structural features of the starting material. This represents a new entrance to biologically interesting polyhydroxylated piperidines having diverse substitutions.