Arene cis-dihydrodiols-useful precursors for the preparation of antimetabolites of the shikimic acid pathway: application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid

Jane L. Humphreys, David J. Lowes, Karen A. Wesson, Roger C. Whitehead

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The synthesis of 6,6-difluoroshikimic acid (11) has been achieved in ten steps from the enantiopure diol 16, which is derived from enzymatic cis-dihydroxylation of iodobenzene. The versatility of the synthetic strategy has been demonstrated by the preparation of the known antimicrobial agent, (6S)-6-fluoroshikimic acid (5). © 2006 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)5099-5108
    Number of pages9
    JournalTetrahedron
    Volume62
    Issue number21
    DOIs
    Publication statusPublished - 22 May 2006

    Keywords

    • Antibacterial agents
    • Fluorination
    • Shikimic acid

    Fingerprint

    Dive into the research topics of 'Arene cis-dihydrodiols-useful precursors for the preparation of antimetabolites of the shikimic acid pathway: application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid'. Together they form a unique fingerprint.

    Cite this