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Reactions of pennogenin and related compounds. Part 2. Reaction of pennogenin 3,17-diacetate with BF3·Et2O

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The rearrangement of pennogenin 3,17-diacetate under the action of BF3-Et2O gives the following products: 20S, 22R, 25R-16α, 17α, 22-(1,t 1′, 1′-ethylidenetrioxy)-22,26-epoxycholest-5-ene-3β-ol-3-acetate and 20S, 25R-16α-0.17α-0.23-(1′,1′,1′-ethylidenedioxy-22,26-epoxycholest-5,22-diene-3β-ol-3-acetate. 2. Acetylation of C17α-OH in the 25R-spirostan series leads to anomalously large effects on the values of chemical shifts of the13C(C16) and (H16) nuclei in their13C and1H NMR spectra.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    L. J. Strigina, V. A. Denisenko, V. A. Rashkes & A. V. Kamernitskii

  2. Pacific Institute of Bioorganic Chemistry, Far-East Scientific Center, Vladivostok

    L. J. Strigina, V. A. Denisenko, V. A. Rashkes & A. V. Kamernitskii

  3. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent

    L. J. Strigina, V. A. Denisenko, V. A. Rashkes & A. V. Kamernitskii

Authors
  1. L. J. Strigina
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  2. V. A. Denisenko
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  3. V. A. Rashkes
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  4. A. V. Kamernitskii
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 431–436, February, 1987.

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Strigina, L.J., Denisenko, V.A., Rashkes, V.A. et al. Reactions of pennogenin and related compounds. Part 2. Reaction of pennogenin 3,17-diacetate with BF3·Et2O. Russ Chem Bull 36, 389–394 (1987). https://doi.org/10.1007/BF00959389

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  • DOI: https://doi.org/10.1007/BF00959389

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