Stereoselective bromination of β-ribofuranosyl amide. Enantioselective synthesis of (+)-hydantocidin

Abstract

The synthesis of hydantocidin, a potent herbicidal natural product, is highlighted by a stereoselective bromination of β-D-ribofuranosyl amide to give only the α-bromo β-amide and subsequent spirocyclization about the anomeric position with silver cyanate to form the hydantoin moiety.