Synthesis of new thio corticosteroids including 1α,9α-epidithio-11β,17α,21-trihydroxy-16β-methylpregn-4-ene-3,20-dione

Abstract

Reaction of 3-keto 1α,5α-epidithio steroids with sulphuryl dichloride cleaves the tertiary carbon-sulphur bond to afford a Δ⁴-3-keto 1α-thiosulphenyl chloride which may be captured by various nucleophiles, in situ, to afford a number of novel 1α-substituted corticosteroid analogues. Intramolecular capture by a Δ⁹⁽¹¹⁾-double bond leads to a synthesis of the title compound.