198217-02-6Relevant articles and documents
Total synthesis of acinetoferrin
Wang, Queenie Xianghong,Phanstiel IV, Otto
, p. 1491 - 1495 (2007/10/03)
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.