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Updated: Apr 18, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Effective and mild method for converting 3β-hydroxysteroids to 3-keto steroids via DDQ/TEMPO
Wu Zhang1, Dan Pan1, Aiqun Wu1
1College of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Key Laboratory of Development and Application of Forest Chemicals of Guangxi, Nanning 530006, China.
Abstract:
A mild and efficient oxidation of 3β-hydroxysteroids to the corresponding 3-keto steroids can be carried out at room temperature, using DDQ in the presence of catalytic TEMPO. Oxidation of saturated 3β-hydroxysteroids gave the corresponding ketones in excellent yield. The 5-unsaturated 3β-hydroxysteroids are oxidized selectively to 4-en-3-one or 4,6-diene-3-one derivatives according to the amount of DDQ in reaction. This is a good method for the synthesis of 4,6-diene-3-one from the corresponding 3β-hydroxy-5-ene steroids. Meanwhile, configurations of the oxidation compounds 2a, 2b, 3b, 2c, 2f and 2g were identified by X-ray diffraction. A possible mechanism is presented and discussed.
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