Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Tetracyclines. Communication 18. Synthesis of 2- and 3-substituted 9-keto-1,2,3,4,4a,9,9a,10-octahydroanthracenes

  • 22 Accesses

Summary

  1. 1.

    An investigation was made of ways of synthesizing 10-keto-1,2,3,4,4a,9,9a,10-octahydroanthracenes containing various functional groups in the 2- and 3-positions.

  2. 2.

    The compounds obtained may serve as intermediaries in the synthesis of substances related to 6-deoxy-tetracyclines.

This is a preview of subscription content, log in to check access.

Literature cited

  1. 1.

    M. N. Kolosov, A. I. Gurevich and Yu. B. Gurevich and Yu. B. Shvetsov, Izv. AN SSSR. Otd. khim. n.1963, 701.

  2. 2.

    M. N. Kolosov, M. M. Shemyakin, A. S. Khokhlov, and Yu. A. Berlin, in the book “Chemistry of Antibiotics” [in Russian], Moscow, 1961, Vol. 1, Chapter III.

  3. 3.

    M. M. Shemyakin, M. N. Kolosov, M. G. Karapetyan, and E. S. Chaman, Dokl. AN SSSR112, 669 (1957).

  4. 4.

    M. N. Kolosov, V. N. Dobrynin, A. I. Gurevich, and M. G. Karapetyan, Izv. AN SSSR. Otd. khim. n.1963, 696.

  5. 5.

    E. L. Martin, J. Amer. Chem. Soc.58, 1438 (1936).

  6. 6.

    D. J. Cram and J. A. Abd Elhafez, J. Amer. Chem. Soc.74, 5828 (1952).

  7. 7.

    S. M. Bloom, J. Amer. Chem. Soc.80, 6280 (1958).

  8. 8.

    M. S. Newman and P. H. Wise, J. Amer. Chem. Soc.63, 2109 (1941); M. Gates and C. L. Dickinson, J. Amer. Chem. Soc.79, 1398 (1957).

  9. 9.

    Yu. A. Arbuzov, M. N. Kolosov, Yu. A. Ovchinnikov, and M. M. Shemyakin, Izv. AN SSSR. Otd. khim. n.1961, 377.

  10. 10.

    L. F. Fieser and F. C. Novello, J. Amer. Chem. Soc.64, 802 (1942).

  11. 11.

    Yu. P. Volkov, M. N. Kolosov, V. G. Korobko, and M. M. Shemyakin, Izv. AN SSSR. Otd. khim. n.1964 (in the press).

  12. 12.

    M. M. Shemyakin, M. N. Kolosov, M. G. Karapetyan, Hsiey Yü-yüan, and V. V. Onoprienko, Izv. AN SSSR. Otd. khim. n.1964 (in the press).

  13. 13.

    G. Baddeley, G. Holt, and S. W. Makar, J. Chem. Soc.1952, 3289.

  14. 14.

    Huang-Minlon, J. Amer. Chem. Soc.68, 2487 (1946).

  15. 15.

    J. W. Cook, C. L. Hewett, and C. A. Lawrence, J. Chem. Soc.1936, 71.

Download references

Author information

Additional information

For Communication 17 see [1].

The authors thank L. B. Senyavina for carrying out infrared-spectrum measurements.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Arbuzov, Y.A., Bolesov, I.G., Bregadze, V.I. et al. Tetracyclines. Communication 18. Synthesis of 2- and 3-substituted 9-keto-1,2,3,4,4a,9,9a,10-octahydroanthracenes. Russ Chem Bull 13, 284–292 (1964). https://doi.org/10.1007/BF00853687

Download citation

Keywords

  • Tetracycline