Total synthesis of acinetoferrin
Abbreviated Journal Title
J. Org. Chem.
CHELATION-THERAPY; SCHIZOKINEN; NANNOCHELIN; SIDEROPHORE; Chemistry, Organic
The total synthesis of a novel siderophore, acinetoferrin, is described. The key transformation involves the tandem oxidation and acylation of the N-3-amino group of N-1-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 alpha,beta-unsaturated hydroxamic acids.
Journal of Organic Chemistry
"Total synthesis of acinetoferrin" (1998). Faculty Bibliography 1990s. 2489.