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

A.C. Hunter, S.M. Priest

Research output: Contribution to journalArticle

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.
Original languageEnglish
Pages (from-to)30-33
Number of pages4
JournalSteroids
Volume71
Issue number1
Publication statusPublished - Jan 2006

Keywords

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

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