A study was made of the homolytic and acid-catalyzed addition of thioacetic acid to 16α,17α-epoxy-Δ5-pregnen-3β-o1-20-one 3-acetate.
In both cases the reaction goes in a structurally selective manner that is contrary to the Markovnikov rule, but not stereospecifically, with the formation of the 3,6-diacetates of 6ξ-thiol-5α-pregnan-3β-o1-20-one epimeric at C6.
The structure and stereochemistry of the obtained thioacetates were established by physical and chemical methods.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2558–2561, November, 1971.
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Akhrem, A.A., Turuta, A.M. & Prokof'ev, E.P. Transformed steroids Communication 38. Stereochemical and structural direction of the addition of thioacetic acid to 16α,17α-epoxy-Δ5-pregnen-3β-ol-20-one 3-acetate. Russ Chem Bull 20, 2422–2425 (1971). https://doi.org/10.1007/BF00854326
- Chemical Method
- Structural Direction
- Selective Manner