A concise method for the preparation of deuterium-labeled cortisone: Synthesis of [6,7-2H]cortisone

A method is described for the synthesis of isotopically labeled cortisone from commercially available cortisone acetate through a Δ4,6-dieneone. Direct deuteration of the dienone acetate with various catalysts in different solvent systems failed to give an isolable product. Initial hydrolysis of the side-chain ester of the Δ4,6-dieneone and subsequent derivatization gave the key intermediate, 17α,20;20,21-bismethylenedioxy-pregna-4,6-diene-3,11-dione, which could be satisfactorily deuterated to the desired product. The availability of [6,7-2H]cortisone will provide a tool for the future study of the metabolism of cortisone in human tissues.