Title

Total synthesis of acinetoferrin

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.

Publication Date

3-6-1998

Publication Title

Journal of Organic Chemistry

Volume

63

Issue

5

Number of Pages

1491-1495

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1021/jo9717144

Socpus ID

0032489410 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/0032489410

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