ChemInform Abstract: Synthesis of 10β-Oxiranyl and 10β-Thiiranyl Steroids.
Abstract
Methylenation of the protected oxoandrostenediol (I) with dimethylsulfoxonium methylide or dimethylsulfonium methylide and subsequent deprotection yield the diastereomeric 10β-oxiranylestra-5-ene-3β,17β-diols (III).
ChemInform Abstract
Methylenation of the protected oxoandrostenediol (I) with dimethylsulfoxonium methylide or dimethylsulfonium methylide and subsequent deprotection yield the diastereomeric 10β-oxiranylestra-5-ene-3β,17β-diols (III). These undergo Oppenauer oxidation to form the diones (V) which are sulfurized with triphenylphosphine sulfide (VI) under inversion of the configuration, producing the thiiranyl derivatives (VII). When the sulfurization is performed in the presence of trifluoroacetic acid (VIII), the cyclic thioethers (IX) are obtained.
