Synthesis of 20-hydroxy-17,21 -cyclopregnane derivatives: potential C-20 oxo steroid oxidoreductase inhibitors

Abstract

20α- and 20β-Hydroxy-17α,21α-cyclopregnane derivatives, potential mechanism-based-inhibitors of 20α- and 20β-steroid oxidoreductases, have been synthesized by conversion of the steroid 17β-aldehyde into the 20-tert-butyldimethylsilyl enol ether followed by addition of methylene prepared from the Simmons–Smith reagent. Enzyme inhibition studies show that neither 20α- nor 20β-hydroxy-17α,21 α-cyclopregn-4-en-3-one were inhibitors of the respective enzymes from Streptomyces hydrogenans.