Synthetic studies on (+)-hydantocidin (3): A new synthetic method for construction of the spiro-hydantoin ring at the anomeric position of D-ribofuranose

Article abstract of DOI:10.1016/S0040-4020(01)96124-1

A facile synthetic route for the large-scale preparation of a herbicidal natural product, (+)-hydantocidin is described. The protected D-psicose 6, prepared in five steps from D-fructose, was stereospecifically converted to azido-amide 14 by N-glycosidation (TMSN₃/TMSOTf), oxidation and animation. Hydantoin ring-construction on 14 was achieved by aza-Wittig reaction (PBu₃/CO₂/CH₃CN) to give 16 without epimerization at the anomeric center. After acetylation, stepwise deprotection of 24 afforded (+)-hydantocidin 1 in 16% overall yield from D-fructose.