A SIMPLE 2-STEP METHOD FOR THE CONVERSION OF [H-3] CORTISOL TO [H-3] 11-KETOTESTOSTERONE

Despite the existence of several protocols, problems appear to persist in the small scale chemical synthesis of radiolabeled 11-ketotestoste rone from cortisol. We investigated the possibilities of using the mil d oxidant pyridinium dichromate for the oxidative cleavage of the dihy droxyacetone side chain of cortisol and 17 beta-hydroxysteroid dehydro genase for the subsequent reduction of the resulting 17-keto group. Ou r protocol has resulted in consistently high yields of both the interm ediate, adrenosterone (70-80%), and the product, 11-ketotestosterone ( up to 60%). This, taken together with the convenience and relatively l ow cost of our method, recommends the protocol for its use for the syn thesis of [H-3]-11-ketotestosterone for endocrine studies. (C) 1997 by Elsevier Science Inc.