Regioselective oxyfunctionalization of unactivated carbons in steroids by a model of cytochrome P-450:: Osmiumporphyrin complex/tert-butyl hydroperoxide system

tert-Butyl hydroperoxide catalyzed by (5,10,15,20-tetramesitylporphyrinate) osmium(II) carbonyl [Os(TMP)CO] complex was found to be a highly efficient versatile oxidant for C-H carbons in steroid substrates. When reacted with representative steroids with an estrane, pregnane, 5 beta-cholane, or 5 alpha-cholestane structure, regioselective oxyfunctionalization and/or oxidative degradation occurred to give a variety of novel and uncommon derivatives in one step.