Russian Chemical Bulletin

, Volume 59, Issue 10, pp 1930–1936 | Cite as

Oxidative and hydrolytic cleavage of cyclopropane and spirocyclobutane derivatives of 6,8-dioxabicyclo[3.2.1]octane, the products of transformation of levoglucosenone

  • R. A. Novikov
  • R. R. Rafikov
  • E. V. Shulishov
  • Yu. V. Tomilov
Full Articles
First Online:
Received:
Revised:
  • 109 Downloads

Abstract

A new method for the synthesis of (1R,4S,5S)-4-hydroxymethyl-3-oxabicyclo[3.1.0]hexan2-one, the cyclopropane analog of (S)-5-hydroxypent-2-en-4-olide, has been suggested based on oxidation of (1S,2S,4R,6R)-7,9-dioxatricyclo[4.2.1.02,4]nonan-5-one. Oxidation of cyclobutanones, spirojoined with the fragments of 6,8-dioxabicyclo[3.2.1]oct-2-ene, 6,8-dioxabicyclo[3.2.1]octane (at position 4), or 7,9-dioxatricyclo[4.2.1.02,4]nonane (at position 5), upon the action of m-chloroperoxybenzoic acid or the KMnO4-H2SO4-H2O system leads to the corresponding spirojoined butanolides in 73–85% yields. The same cyclobutanones easily undergo the four-membered ring opening upon the action of dilute H2SO4 at 50–90 °C to form 6,8-dioxabicyclo[3.2.1]octane-4- or 7,9-dioxatricyclo[4.2.1.02,4]nonane-5-propionic acid.

Key words

7,9-dioxatricyclo[4.2.1.02,4]nonan-5-one 3-oxabicyclo[3.1.0]hexan-2-ones spiro{6,8-dioxabicyclo[3.2.1]octane-4,2′-cyclobutanones} spiro compounds γ-lactones oxidation hydration cyclobutanones levoglucosenone 
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. S. Miftakhov, F. A. Valeev, I. N. Gaisina, Usp. Khim., 1993, 62, 922 [Russ. Chem. Rev. (Engl. Transl.), 1993, 62].Google Scholar
  2. 2.
    K. Koseki, T. Ebata, H. Kawakami, H. Matasushita, Y. Naoi, K. Itoh, Heterocycles, 1990, 31, 423.CrossRefGoogle Scholar
  3. 3.
    Eur. Pat. 411403; Chem Abstr., 1991, 114, 185135m.Google Scholar
  4. 4.
    H. Kawakami, T. Ebata, K. Koseki, K. Matsumoto, H. Matasushita, Y. Naoi, K. Itoh, Heterocycles, 1990, 31, 2041.CrossRefGoogle Scholar
  5. 5.
    T. Ebata, K. Matsumoto, H. Yoshikoshi, K. Koseki, H. Kawakami, H. Matasushita, Heterocycles, 1990, 31, 1585.CrossRefGoogle Scholar
  6. 6.
    K. Matsumoto, T. Ebata, K. Koseki, K. Okano, H. Kawakami, H. Matasushita, Bull. Chem. Soc. Jpn., 1995, 68, 670.CrossRefGoogle Scholar
  7. 7.
    F. A. Valeev, I. N. Gaisina, M. S. Miftakhov, G. A. Tolstikov, Zh. Org. Khim., 1993, 29, 105 [Russ. J. Org. Chem. (Engl. Transl.), 1993, 29].Google Scholar
  8. 8.
    F. A. Valeev, I. N. Gaisina, M. S. Miftakhov, Zh. Org. Khim., 1996, 32, 1365 [Russ. J. Org. Chem. (Engl. Transl.), 1996, 32, 1319].Google Scholar
  9. 9.
    A. V. Samet, D. N. Lutov, L. D. Konyushkin, Yu. A. Strelenko, V. V. Semenov, Tetrahedron: Asymmetry, 2008, 19, 691.CrossRefGoogle Scholar
  10. 10.
    A. V. Samet, A. M. Shestopalov, D. N. Lutov, L. A. Rodinovskaya, L. A. Shestopalov, V. V. Semenov, Tetrahedron: Asymmetry, 2007, 18, 1986.CrossRefGoogle Scholar
  11. 11.
    R. A. Novikov, R. R. Rafikov, E. V. Shulishov, L. D. Konyushkin, V. V. Semenov, Yu. V. Tomilov, Izv. Akad. Nauk, Ser. Khim., 2009, 325 [Russ. Chem. Bull., Int. Ed., 2009, 58, 327].Google Scholar
  12. 12.
    M. Martin-Vila, N. Hanafi, J. M. Jimenez, A. Alvarez-Larena, J. F. Piniella, V. Branchadell, A. Oliva, R. M. Ortuno, J. Org. Chem., 1998, 63, 3581.CrossRefGoogle Scholar
  13. 13.
    Y. Zhao, T. Yang, M. Lee, D. Lee, M. G. Newton, C. K. Chu, J. Org. Chem., 1995, 60, 5236.CrossRefGoogle Scholar
  14. 14.
    R. R. Rafikov, R. A. Novikov, E. V. Shulishov, L. D. Konyushkin, V. V. Semenov, Yu. V. Tomilov, Izv. Akad. Nauk, Ser. Khim., 2009, 1866 [Russ. Chem. Bull., Int. Ed., 2009, 58, 1927].Google Scholar
  15. 15.
    R. R. Rafikov, R. A. Novikov, E. V. Shulishov, Yu. V. Tomilov, Izv. Akad. Nauk, Ser. Khim., 2009, 2371 [Russ. Chem. Bull., Int. Ed., 2009, 58, 2449].Google Scholar
  16. 16.
    G. R. Krow, Organic Reactions, John Wiley and Sons, New York, 1993, 43, p. 251.Google Scholar
  17. 17.
    L. M. Mikkelsen, S. L. Krintel, J. Jiménez-Barbero, T. Skrydstrup, J. Org. Chem., 2002, 67, 6297.CrossRefGoogle Scholar
  18. 18.
    M. E. Jung, M. Kiankarimi, J. Org. Chem., 1998, 63, 8133.CrossRefGoogle Scholar
  19. 19.
    J. Attenburrow, A. F. B. Cameron, J. H. Chapman, R. M. Evans, B. A. Hems, A. B. A. Jansen, T. Walker, J. Chem. Soc., 1952, 1094.Google Scholar

Copyright information

© Springer Science+Business Media, Inc.  2010

Authors and Affiliations

  • R. A. Novikov
    • 1
  • R. R. Rafikov
    • 1
  • E. V. Shulishov
    • 1
  • Yu. V. Tomilov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations