Synthesis of Corticosteroid Haptens Possessing the Bridge at the C-4 Position

Abstract

In order to obtain specific antisera for use in radioimmunoassay and enzyme immunoassay, new haptens of cortisol, 11-deoxycortisol and cortisone were prepared. The synthesis of the 4-hemisuccinates of 4-hydroxycortisol and 4-hydroxy-11-deoxycortisol was accomplished by employing suitably protected 21-mono-tert-butyldimethylsilyl ethers of the 4-hydroxysteroids as key intermediates. As another type of hapten, the 4-carboxy-methylthio derivatives of corticosteroids were prepared by base-catalyzed ring opening of the 4, 5-epoxide with mercaptoacetic acid. In addition, the preparation of related haptens is described.