Conclusions
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1.
We have carried out the syntheses of 8α, 14α- and 8β, 14β-epoxy-12-ketocholanic acids and their 3-acyl derivatives.
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2.
β-Epoxides by the action of proton acids and Lewis acids are converted to the 7,14 choladienes, and by the action of boron trifluoride in acetic anhydride, to the product acylated at C11,α-epoxides under proton acid conditions yield 8,14-dienes, and under “backbone” rearrangement conditions with boron trifluoride in benzene, to the rearrangement product, the methyl ester of 3α-methoxycarbonyloxy-5β-chola-9(11), 13(17)-diene-14ξ-methyl-12-on-24-oic acid. The Δ13(17) bond was reduced by hydrogenation over Adams catalyst.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2596–2601, November, 1984.
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Kamernitskii, A.V., Reshetova, I.G., Chernov, S.V. et al. Transformations of steroids Communication 139. Synthesis and rearrangement of 8, 14,-epoxy-12-keto-cholanic acids. Russ Chem Bull 33, 2377–2382 (1984). https://doi.org/10.1007/BF00948857
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DOI: https://doi.org/10.1007/BF00948857