Title

Total synthesis of acinetoferrin

Authors

Authors

Q. X. H. Wang;O. Phanstiel

Comments

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Abbreviated Journal Title

J. Org. Chem.

Keywords

CHELATION-THERAPY; SCHIZOKINEN; NANNOCHELIN; SIDEROPHORE; Chemistry, Organic

Abstract

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 Title

Journal of Organic Chemistry

Volume

63

Issue/Number

5

Publication Date

1-1-1998

Document Type

Article

Language

English

First Page

1491

Last Page

1495

WOS Identifier

WOS:000072564300020

ISSN

0022-3263

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