Synthesis and radical oxidation of steroidal 1-oxo-5α-alcohols

Abstract

A new synthetic approach is described for the preparation of steroidal 1-oxo-5α-alcohols. A key step in the synthesis was the [2,3]sigmatropic rearrangement of allylic 3α-selenide ensuring the introduction of the desired functional groups at C-1 and C-5. The radical oxidation of 1-oxo-5α-alcohol was shown to proceed with the formation of 5,10-seco steroid. Its structural assignment was based on NMR and CD spectroscopic studies. ©ARKAT-USA, Inc.