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
2005; Elsevier BV; Volume: 71; Issue: 1 Linguagem: Inglês
10.1016/j.steroids.2005.07.007
ISSN1878-5867
AutoresA. Christy Hunter, Shelley-Marie Priest,
Tópico(s)Bioactive Compounds and Antitumor Agents
ResumoSteroids 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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