Abstract

The total synthesis of a novel siderophore, acinetoferrin, is described. The key transformation involves the tandem oxidation and acylation of the N3-amino group of N1-BOC propane diamine prior to coupling with the external carboxyls of citric acid. A “one-pot−two-step” reaction converted a primary amine (RNH2) into a O-benzoyl hydroxamate (i.e., RN(OOCPh)COR‘) in good yield (68%). These studies demonstrated the utility of the O-benzoyl protecting group in the synthesis of α,β-unsaturated hydroxamic acids.

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