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Russian Journal of Organic Chemistry

, Volume 54, Issue 10, pp 1463–1468 | Cite as

Eleuthesides and Their Analogs: XIII. Synthesis of Bicyclo[6.2.1]undecane System from Cyclohex-2-en-1-one

  • B. T. Sharipov
  • A. N. Davydova
  • F. A. Valeev
Article
  • 8 Downloads

Abstract

A short synthetic route to bicyclo[6.2.1]undec-9-ene-2,6-dione has been developed on the basis of retro-aldol reaction of 7-hydroxytricyclo[6.2.1.02,7]undec-9-en-3-one obtained from the Diels–Alder adducts of 3-tosylcyclohex-2-en-1-one with cyclopentadiene.

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References

  1. 1.
    Sharipov, B.T., Pershin, A.A., Salikhov, Sh.M., and Valeev, F.A., Russ. J. Org. Chem., 2016, vol. 52, p. 978.CrossRefGoogle Scholar
  2. 2.
    Lindel, T., Jensen, P.R., Fenical, W., Long, B.H., Casazza, A.M., Carboni, J., and Fairchild, C.R., J. Am. Chem. Soc., 1997, vol. 119, p. 8744.CrossRefGoogle Scholar
  3. 3.
    Alam, M., Sharma, P., Zektzer, A.S., Martin, G.E., Ji, X., and van der Helm, D., J. Org. Chem., 1989, vol. 54, p. 1896.CrossRefGoogle Scholar
  4. 4.
    Vichnewski, W., Takahashi, A.M., Nasi, A.M.T., Gonçalves, D.C.R.G., Dias, D.A., Lopes, J.N.C., Goedken, V.L., Gutiérrez, A.B., and Herz, W., Phytochemistry, 1989, vol. 28, p. 1441.CrossRefGoogle Scholar
  5. 5.
    Leon, F.M. and Carretero, J.C., Tetrahedron Lett., 1991, vol. 32, p. 5405.CrossRefGoogle Scholar
  6. 6.
    Kienzle, F. and Minder, R.E., Helv. Chim. Acta, 1987, vol. 70, p. 1537.CrossRefGoogle Scholar
  7. 7.
    Najera, C., Baldo, B., and Yus, M., J. Chem. Soc., Perkin Trans. 1, 1988, p. 1029.Google Scholar
  8. 8.
    Das, B., Lingaiah, M., Damodar, K., and Bhunia, N., Synthesis, 2011, p. 2941.Google Scholar
  9. 9.
    Shi, Y.-L. and Shi, M., Org. Biomol. Chem., 2005, vol. 3, p. 1620.CrossRefGoogle Scholar
  10. 10.
    Guan, Z.-H., Zuo, W., Zhao, L.-B., Ren, Z.-H., and Liang, Y.-M., Synthesis, 2007, p. 1465.Google Scholar
  11. 11.
    Zoller, T. and Uguen, D., Eur. J. Org. Chem., 1999, p. 1545.Google Scholar
  12. 12.
    Downey, C.W., Craciun, S., Vivelo, C.A., Neferu, A.M., Mueller, C.J., and Corsi, S., Tetrahedron Lett., 2012, vol. 53, p. 5766.CrossRefGoogle Scholar
  13. 13.
    Wu, C., Yang, P., Fu, Z., Peng, Y., Wang, X., Zhang, Z., Liu, F., Li, W., Li, Z., and He, W., J. Org. Chem., 2016, vol. 81, p. 10 664.Google Scholar
  14. 14.
    Kobayashi, Y., Feng, C., Ikoma, A., Ogawa, N., and Hirotsu, T., Org. Lett., 2014, vol. 16, p. 760.CrossRefGoogle Scholar
  15. 15.
    Constantino, M.G., Beatriz, A., and da Silva, G.V.J., Tetrahedron Lett., 2000, vol. 41, p. 7001.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • B. T. Sharipov
    • 1
  • A. N. Davydova
    • 1
  • F. A. Valeev
    • 1
  1. 1.Institute of Chemistry, Ufa Federal Research CenterRussian Academy of SciencesUfa, BashkortostanRussia

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