Total synthesis of acinetoferrin

    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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