Site-specific dehydrogenation of ring D in steroids

Abstract

The 3α-cholestanyl ester of 5-(4-benzoylphenyl)-valeric acid underwent direct photochemical hydrogen transfer upon irradiation, thereby providing a simple route to Δ¹⁴ and Δ¹⁶ steroids, in 53% yield: a minor proportion of this reaction led to steroidal macrolides.