An efficient one-pot synthesis generating 4-ene-3,6-dione functionalised steroids from steroidal 5-en-3beta-ols using a modified Jones oxidation methodology.
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.
Hunter
A Christy
AC
Molecular Targeting and Polymer Toxicology Group, School of Pharmacy and Biomolecular Sciences, University of Brighton, East Sussex BN2 4GJ, UK. c.hunter@bton.ac.uk
Priest
Shelley-Marie
SM
D000735:Androstenedione / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D047072:Aromatase Inhibitors / Q000737:chemistry*; D002782:Cholestenes / Q000737:chemistry*; D015394:Molecular Structure; D011277:Pregnanediones / Q000138:chemical synthesis*; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry*
D047072:Aromatase Inhibitors; D002782:Cholestenes; D011277:Pregnanediones; D013256:Steroids; D000735:Androstenedione