Investigations on sterols XXXVII: New routes to 9,10‐isomers of 6‐dehydroprogesterone

Abstract

Abstract The synthesis of 6‐dehydro‐9β, 10α‐progesterone (IV) from progesterone via irradiation of 3,20‐bis(ethylenedioxy)pregna‐5,7‐diene (II) is described. An analogous synthesis has been accomplished via 3‐(ethylenedioxy)pregna‐5,7‐dien‐20‐one (VI). Pyrolysis of the 9,10‐seco‐bisacetal (IX), a vitamin D analogue, followed by hydrolysis and isomerization, gave the 8α,10α‐isomer of 6‐dehydroprogesterone (XI).