Total synthesis of acinetoferrin

The total synthesis of a novel siderophore, acinetoferrin, is described. The key transformation involves the tandem oxidation and acylation of the [N.sub.3]-amino group of [N.sub.1]-BOC propane diamine prior to coupling with the external carboxyls of citric acid. A 'one-pot-two-step' reaction converted a primary amine (RN[H.sub.2]) into a O-benzoyl hydroxamate (i.e., RN(OOCPh)COR[prime]) in good yield (68%). These studies demonstrated the utility of the O-benzoyl protecting group in the synthesis of [Alpha],[Beta]-unsaturated hydroxamic acids.