Simple synthetic approach to 6-oxa steroids. Synthesis of 6-oxa-5β-pregnane-3,20-dione
Abstract
A two-step synthesis of 19-functionalized 6-oxapregnanes from a 5α,6β-dihydroxypregnane is described. Deoxygenation at C-19 afforded a 6-oxapregnane, which was converted into 6-oxa-5β-pregnane-3,20-dione 7. An insight into the mechanism of formation of the key intermediate, a 5,6-secosteroid, via a hypoiodite type reaction is also given.