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 Delta(4.6)-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 Delta(4.6)-dieneone and subsequent derivatization gave the key intermediate, 17 alpha,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-H-2]cortisone will provide a tool for the future study of the metabolism of cortisone in human tissues. (c) 2005 Elsevier Inc. All rights reserved.