Investigations on sterols XXVI: Synthesis and properties of 6‐substituted 9β,10α‐steroids

Abstract

Abstract The synthesis and properties are described of some 6‐halo‐9β,10α‐pregnane and 6‐halo‐9β,10α‐androstane derivatives containing the 4‐en‐3‐one system. Halogenation at position 6 is accomplished by reaction of the 3‐acetoxy‐3,5‐dienes with perchloryl fluoride, chlorine, bromine or N ‐bromosuccinimide. At the fluorination 6‐hydroxy compounds are obtained as by‐products, the structures of which are proved by alternative synthesis and by conversion into related compounds. The spectral data are discussed in connection with the structural assignments of the 6‐substituents. The biological results are summarized.