Synthesis of (3R*,4R*)-4-acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer and their inhibitory action against influenza virus sialidases

Sean A. Kerrigan, Robin G. Pritchard, Paul W. Smith, Richard J. Stoodley

    Research output: Contribution to journalArticlepeer-review

    Abstract

    (3R*,4R*)-4-Acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer are synthesised in five steps from the Diels-Alder cycloadduct of (E)-1-acetoxy-3-methylbuta-1,3-diene and nitroethene; the former acid is a moderately potent inhibitor of influenza A sialidase. © 2001 Elsevier Science Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)7687-7690
    Number of pages3
    JournalTetrahedron Letters
    Volume42
    Issue number43
    DOIs
    Publication statusPublished - 22 Oct 2001

    Keywords

    • Antivirals
    • Diels-Alder reactions
    • Nitro compounds
    • Oxidation (allylic)

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