An efficient one-pot synthesis generating 4-ene-3,6-dione functionalised steroids from steroidal 5-en-3beta-ols using
A Christy Hunter1, Shelley-Marie Priest
1Molecular Targeting and Polymer Toxicology Group, School of Pharmacy and Biomolecular Sciences, University of Brighton, East Sussex BN2 4GJ, UK. c.hunter@bton.ac.uk
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-3beta-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 (1-2h). The simplicity of this reaction gives significant advantages over previously reported methodologies.
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