An efficient one-pot synthesis generating 4-ene-3,6-dione functionalised steroids from steroidal 5-en-3β-ols using a modified Jones oxidation methodology

A. Christy Hunter, Shelley Marie Priest

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Steroids with 4-ene-3,6-dione functionality have application in natural product chemistry, as synthetic intermediates and as aromatase inhibitors. Here, we report a two-phase oxidation of a range of steroidal 5-en-3β-ols into corresponding 4-ene-3,6-diones using a modified Jones oxidation. The new reaction affords high yields (77-89%) of product in relatively short reaction times (1-2 h). The simplicity of this reaction gives significant advantages over previously reported methodologies. © 2005 Elsevier Inc. All rights reserved.
    Original languageEnglish
    Pages (from-to)30-33
    Number of pages3
    JournalSteroids
    Volume71
    Issue number1
    DOIs
    Publication statusPublished - Jan 2006

    Keywords

    • 4-Ene-3,6-dione
    • Aromatase inhibitor
    • Jones oxidation
    • One-pot synthesis

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