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

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-3 beta-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. (c) 2005 Elsevier Inc. All rights reserved.