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Analogs of corticosteroids

Communication 24. Acyl migration in the cis-1-acetylcyclohexane-1,2-diol series

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Conclusions

  1. 1.

    The acid-catalyzed acylation of secondary monoesters of cis-1-acetylcyclohexan-1,2-diol, in contrast to their uncatalyzed interaction with anhydrides or reaction with the latter in the presence of base, proceeds with migration of the acyl residue from the secondary to a tertiary position.

  2. 2.

    A method of obtaining secondary-tertiary ketodiesters of known structure has been developed.

  3. 3.

    The mechanism of acyl migration in the cis-1-acetylcyclohexan-1,2-diol series was discussed.

  4. 4.

    PMR spectral data of certain cis and trans derivatives of 1-acetylcyclohexan-1,2-diol have been discussed.

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Literature cited

  1. 1.

    A. A. Akhrem and V. N. Dobrynin, Izv. Akad. Nauk SSSR, Ser. Khim., 405 (1967); Dokl. Akad. Nauk SSSR,174, 351 (1967).

  2. 2.

    A. A. Akhrem, A. V. Kamernitskii, V. A. Dubrovskii, and A. M. Moiseenkov, USSR Patent for Appl. No. 907748/23-4, June 25, 1964.

  3. 3.

    A. A. Akhrem, A. V. Kamernitskii, V. A. Dubrovskii, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., 202 (1965).

  4. 4.

    A. A. Akhrem, A. V. Kamernitskii, V. A. Dubrovskii, and A. M. Moiseenkov, Dokl. Akad. Nauk SSSR,162, 811 (1965).

  5. 5.

    V. A. Dubrovskii, A. A. Akhrem, and A. V. Kamernitskii, Izv. Akad. Nauk SSSR, Ser. Khim., 103 (1964).

  6. 6.

    A. A. Akhrem, A. V. Kamernitskii, V. A. Dubrovskii, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1726 (1964).

  7. 7.

    A. A. Akhrem, A. V. Kamernitskii, V. A. Dubrovskii, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., 115 (1967).

  8. 8.

    A. A. Akhrem, A. M. Moiseenkov, A. V. Kamernitskii, and V. A. Dubrovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 109 (1967).

  9. 9.

    A. A. Akhrem and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., 2156 (1966).

  10. 10.

    A. A. Akhrem and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., 2161 (1966).

  11. 11.

    L. F. Fieser and M. Fieser, Steroids [Russian translation], Izd. “Mir” (1964), p. 688; K. Syhora, Collection Czech. Chem. Commun.,26, 1026 (1961).

  12. 12.

    A. A. Akhrem, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 845 (1962).

  13. 13.

    A. M. Moiseenkov and A. A. Akhrem, Izv. Akad. Nauk SSSR, Ser. Khim., 1064 (1963).

  14. 14.

    A. M. Moiseenkov and A. A. Akhrem, Izv, Akad. Nauk SSSR, Ser. Khim., 1446 (1963).

  15. 15.

    L. M. Jackman, Applications of NMR Spectroscopy in Organic Chemistry, Pergamon Press (1959), Chap. 7.

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Additional information

For communications 22 and 23 of this series see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2039–2044, September, 1967.

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Akhrem, A.A., Moiseenkov, A.M., Kaznacheev, Y.D. et al. Analogs of corticosteroids. Russ Chem Bull 16, 1952–1957 (1967). https://doi.org/10.1007/BF00909590

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Keywords

  • Migration
  • Corticosteroid
  • Anhydride
  • Spectral Data
  • Diol