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Russian Journal of Organic Chemistry

, Volume 50, Issue 1, pp 117–127 | Cite as

Eleuthesides and their analogs: V. Medium- and large-ring lactones based on levoglucosenone

  • Yu. A. Khalilova
  • L. V. Spirikhin
  • Sh. M. Salikhov
  • F. A. Valeev
Article

Abstract

Ozonolysis of the bridging double bond in bicyclic enol ethers obtained by the Michael reaction and subsequent intramolecular etherification afforded chiral decanolides fused to a tetrahydropyran ring. Three-step procedures were developed for the synthesis of chiral lactones with medium and large rings via oxidative cleavage with pyridinium chlorochromate of mixed bicyclic ketals which were prepared by treatment with methanolic HCl of Michael adducts derived from levoglucosenone and cyclopenta-, cyclohexa-, cyclohepta-, and cyclododecanone.

Keywords

Petroleum Ether Lactone EtOAc Ozonolysis Colorless Crystal 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Sharipov, B.T., Pershin, A.A., Pilipenko, A.N., Salikhov, Sh.M., and Valeev, F.A., Russ. J. Org. Chem., 2013, vol. 49, p. 1437.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.
    Lindel, T., Angew. Chem., Int. Ed., 1998, vol. 37, p. 774.CrossRefGoogle Scholar
  4. 4.
    Chen, X.-T., Gutteridge, C.E., Bhattacharya, S.K., Zhou, B., Pettus, T.R.R., Hascall, T., and Danishefsky, S.J., Angew. Chem., Int. Ed., 1998, vol. 37, p. 185.CrossRefGoogle Scholar
  5. 5.
    Drager, G., Kirschning, A., Thiericke, R., and Zerlin, M., Nat. Prod. Rep., 1996, p. 365.Google Scholar
  6. 6.
    Hanaki, N., Ishihara, K., Kaino, M., Naruse, Y., and Yamamoto, H., Tetrahedron, 1996, vol. 52, p. 7297.CrossRefGoogle Scholar
  7. 7.
    Borowitz, I.J. and Rapp, R., J. Org. Chem., 1969, vol. 34, p. 1370.CrossRefGoogle Scholar
  8. 8.
    Borowitz, I.J., Williams, G.J., Gross, L., and Rapp, R., J. Org. Chem., 1968, vol. 33, p. 2013.CrossRefGoogle Scholar
  9. 9.
    Posner, G.H., Asirvatham, E., Webb, K.S., and Jew, S.-s., Tetrahedron Lett., 1987, vol. 28, p. 5071.CrossRefGoogle Scholar
  10. 10.
    Posner, G.H., Webb, K.S., Asirvatham, E., Jew, S.-s., and Degl’Innocenti, A., J. Am. Chem. Soc., 1988, vol. 110, p. 4754.CrossRefGoogle Scholar
  11. 11.
    Suginome, H. and Yamada, S., Tetrahedron, 1987, vol. 43, p. 3371.CrossRefGoogle Scholar
  12. 12.
    Suginome, H. and Yamada, S., Tetrahedron Lett., 1985, vol. 26, p. 3715.CrossRefGoogle Scholar
  13. 13.
    Concepcion, J.I., Francisco, C.G., Hernandez, R., Salazar, J.A., and Suarez, E., Tetrahedron Lett., 1984, vol. 25, p. 1953.CrossRefGoogle Scholar
  14. 14.
    Freire, R., Morrero, J.J., Rodriguez, M.S., and Suarez, E., Tetrahedron Lett., 1986, vol. 27, p. 383.CrossRefGoogle Scholar
  15. 15.
    Samet, A.V., Yamskov, A.N., Ugrak, B.I., and Semenov, V.V., Izv. Akad. Nauk, Ser. Khim., 1997, p. 553.Google Scholar
  16. 16.
    Khalilova, Yu.A., Tagirov, A.R., Doronina, O.Yu., Spirikhin, L.V., Salikhov, Sh.M., and Valeev, F.A., Russ. J. Org. Chem., 2014, vol. 50, p. 110.CrossRefGoogle Scholar
  17. 17.
    Kwatr, H. and Nickle, J.H., J. Am. Chem. Soc., 1976, vol. 98, p. 2881.CrossRefGoogle Scholar
  18. 18.
    Stork, G. and Landesman, H.K., J. Am. Chem. Soc., 1956, vol. 78, p. 5129.CrossRefGoogle Scholar
  19. 19.
    Braer, A., WO Patent no. 2002 059 101, 2002.Google Scholar
  20. 20.
    Nicolaou, K.C., Roschangar, F., and Vourloumis, D., Angew. Chem., Int. Ed., 1998, vol. 37, p. 2014.CrossRefGoogle Scholar
  21. 21.
    Khalilova, Yu.A., Krasnoslobodtseva, O.Yu., Sharipov, B.T., Galimova, Yu.S., and Valeev, F.A., Vestn. Bashkir. Gos. Univ., 2011, no. 16, p. 22.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  • Yu. A. Khalilova
    • 1
  • L. V. Spirikhin
    • 1
  • Sh. M. Salikhov
    • 1
  • F. A. Valeev
    • 1
  1. 1.Institute of Organic Chemistry, Ufa Research CenterRussian Academy of SciencesUfaBashkortostan, Russia

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