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Stereoselective preparation of mono- and bis-derivatives of pentacyclo[6.3.0.02,6.03,10.05,9] undecane (D 3-trishomocubane)

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Central European Journal of Chemistry

Abstract

The rearrangement of easily accessible Cookson’s diketone with chlorosulfonic acid in chloroform followed by the acidic hydrolysis gave 6-chloro-7-hydroxy-dichloropentacyclo[6.3.0.02,6.03,10.05,9]undecane-4-one, whose syn-stereochemistry was assigned through the X-ray crystal structure analysis. This key structure was used for the stereoselective synthesis of the D 3-trishomocubane derivatives as well as for the preparation of potential drugs bearing hydroxy- and amino-functional groups. A new multigram preparative synthesis of D 3-trishomocubane was developed.

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References

  1. G.R. Underwood, B. Ramamoorthy, Tetrahedron Lett. 11, 4125 (1970)

    Article  Google Scholar 

  2. D.M. Ho, R.A. Pascal, Chem. Mater. 5, 1358 (1993)

    Article  CAS  Google Scholar 

  3. A.V. Gaidai, D.M. Volochnyuk, O.V. Shishkin, A.A. Fokin, I.A. Levandovskiy, T.E. Shubina, Synthesis 810 (2012)

  4. A. Sklyarova, V. Rodionov, C. Parsons, G. Quack, P. Schreiner, A. Fokin, Med. Chem. Res. 360 (2012)

  5. G.J. Kent, S.A. Godleski, E. Osawa, P.v.R. Schleyer, J. Org. Chem. 42, 3852 (1977)

    Article  CAS  Google Scholar 

  6. S.A. Godleski, P.v.R. Schleyer, E. Osawa, G.J. Kent, J. Chem. Soc., Chem. Commun. 976 (1974)

  7. K. Naemura, T. Fujii, H. Chikamatsu, Chem. Lett. 15, 923 (1986)

    Article  Google Scholar 

  8. D.W. Oliver, T.G. Dekker, S. Afr. J. Chem. 32, 45 (1979)

    Google Scholar 

  9. M. Nakazaki, K. Naemura, N. Arashiba, J. Org. Chem. 43, 689 (1978)

    Article  CAS  Google Scholar 

  10. P.E. Eaton, B. Leipzig, J. Org. Chem. 43, 2483 (1978)

    Article  CAS  Google Scholar 

  11. M. Nakazaki, H. Chikamatsu, K. Naemura, T. Suzuki, M. Iwasaki, Y. Sasaki, T. Fujii, J. Org. Chem. 46, 2726 (1981)

    Article  CAS  Google Scholar 

  12. R. C. Cookson, E. Crundwell, R.R. Hill, J. Hudec, J. Chem. Soc. 3062 (1964)

  13. G.A. Tolstikov, B.M. Lerman, F.Z. Galin, Zh. Org. Khim. 12, 1133 (1976)

    CAS  Google Scholar 

  14. D.I. Sharapa, A.V. Gayday, A.G. Mitlenko, I.A. Levandovskiy, T.E. Shubina, Eur. J. Org. Chem. 2011, 2554 (2011)

    Article  Google Scholar 

  15. G. Helmchen, G. Staiger, Angew. Chem. Int. Ed. 16, 116 (1977)

    Article  Google Scholar 

  16. G.A. Tolstikov, B.M. Lerman, F.Z. Galin, Y.T. Struchkov, V.G. Andrianov, Tetrahedron Lett. 19, 4145 (1978)

    Article  Google Scholar 

  17. D.W. Oliver, T.G. Dekker, F.O. Snyckers, T.G. Fourie, J. Med. Chem. 34, 851 (1991)

    Article  CAS  Google Scholar 

  18. A.J.M. Carpy, D.W. Oliver, Helv. Chim. Acta 77, 543 (1994)

    Article  CAS  Google Scholar 

  19. C. Zlotogorski, J. Blum, E. Osawa, H. Schwarz, G. Hoehne, J. Org. Chem. 49, 971 (1984).

    Article  CAS  Google Scholar 

  20. V.T. Nguyen, P.D. Ahn, R. Bishop, M.L. Scudder, D.C. Craig, Eur. J. Org. Chem. 4489 (2001)

  21. C.J. Van der Schyf, W.J. Geldenhuys, Neurotherapeutics 6, 175 (2009)

    Article  Google Scholar 

  22. W.J. Geldenhuys, S.F. Mala, J.R. Bloomquist, A.P. Marchand, C.J.V.d. Schyf, Med. Res. Rev. 25, 21 (2005)

    Article  CAS  Google Scholar 

  23. G.M. Sheldrick, Programs for the Solution of Crystal Structures, SHELXS97 and SHELXL97 (University of Gottingen, Germany, 1997)

    Google Scholar 

  24. G. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 64, 112 (2008)

    Article  CAS  Google Scholar 

  25. G. Mehta, A.V. Reddy, A. Srikrishna, J. Chem. Soc., Perkin Trans. 291 (1986)

  26. E.C. Smith, J.C. Barborak, J. Org. Chem. 41, 1433 (1976)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Organic Chemistry, Kiev Polytechnic Institute, 03056, Kiev, Ukraine

    Anastasiia M. Mishura, Anna S. Sklyarova, Dmitriy I. Sharapa, Igor’ A. Levandovsky, Andrey A. Fokin & Vladimir N. Rodionov

  2. Institute of Organic Chemistry, Justus-Liebig University, D-35392, Giessen, Germany

    Michael Serafin

Authors
  1. Anastasiia M. Mishura
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  2. Anna S. Sklyarova
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  3. Dmitriy I. Sharapa
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  4. Igor’ A. Levandovsky
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  5. Michael Serafin
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  6. Andrey A. Fokin
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  7. Vladimir N. Rodionov
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Correspondence to Vladimir N. Rodionov.

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Mishura, A.M., Sklyarova, A.S., Sharapa, D.I. et al. Stereoselective preparation of mono- and bis-derivatives of pentacyclo[6.3.0.02,6.03,10.05,9] undecane (D 3-trishomocubane). cent.eur.j.chem. 11, 2144–2150 (2013). https://doi.org/10.2478/s11532-013-0339-8

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  • DOI: https://doi.org/10.2478/s11532-013-0339-8

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