Synthesis of 11-deoxy-18-hydroxycorticosterone and 18-hydroxycorticosterone 21-acetates

Abstract

Functionalisation of the steroid 13-methyl group by nitrite photolysis in the presence of oxygen affords 18-nitrates. The 18-nitrate system provides convenient protection for the 18-hydroxy-group and generates the latter on reduction with zinc under neutral conditions. In this way, convenient syntheses of 11-deoxy-18-hydroxycorticosterone (Xi) and of 18-hydroxycorticosterone (XIIIg) have been completed.