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Transformed steroids 117. Synthesis of 5α-hydroxy-6-oxosteroids with a δ-lactone ring E

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Abstract

The paper is devoted to the synthesis of steroidal 5α-hydroxy-6-oxolactones from ethyl esters of 5,6-dienic acids. By epoxidating the latter it has been shown that, in addition to the usual formation of 5,6-oxides, opening of the 16α, 17-oxide ring initially formed takes place and this is accompanied by intramolecular cyclization to a 17,20-dihydroxy-β-lactone. The trans-opening of the 5α,6α-epoxide in the epoxy-δ-lactone and subsequent oxidation with N-bromosuccinimide has led to a new representative of steroidal δ-lactones — the 23,16-δ-lactone of the 3-acetate of 3β, 5α, 16β, 17α, 20ξ-pentahydroxy-6-oxo-24-norcholan-23-oic acid.

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Literature cited

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Authors
  1. A. V. Kamernitskii
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  2. V. A. Krivoruchko
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  3. I. G. Reshetova
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Additional information

N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 208–213, March–April, 1980.

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Kamernitskii, A.V., Krivoruchko, V.A. & Reshetova, I.G. Transformed steroids 117. Synthesis of 5α-hydroxy-6-oxosteroids with a δ-lactone ring E. Chem Nat Compd 16, 162–166 (1980). https://doi.org/10.1007/BF00638777

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  • DOI: https://doi.org/10.1007/BF00638777

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