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

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Steroids
Oxidation
Aromatase Inhibitors
Biological Products

Keywords

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

Cite this

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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.",
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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. / Hunter, A.C.; Priest, S.M.

In: Steroids, Vol. 71, No. 1, 01.2006, p. 30-33.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 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

AU - Hunter, A.C.

AU - Priest, S.M.

PY - 2006/1

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N2 - 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.

AB - 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.

KW - 4-Ene-3,6-dione

KW - Jones oxidation

KW - One-pot synthesis

KW - Aromatase inhibitor

M3 - Article

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EP - 33

JO - Steroids

JF - Steroids

SN - 0039-128X

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