Philip M. Harrington

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.

An unusual synthesis of nicotinamides

Reaction of 2,3-pyridinedicarboxylic anhydride (1) with a substituted aniline (2) in acetic acid gave rise to a mixture of two products. These two products were identified as the cyclic imide pyrrolo[3,4-b]pyridine derivative (4) and nicotinamide (5). A mechanistic scheme consisted with empirical observations is proposed