Skip to main content
SpringerLink
Log in

Anomalous ozonolysis product of 3β,28-di-O-acetyl-29-norlupan-20-one-O-methyloxime

  • Published:
Chemistry of Natural Compounds Aims and scope

Ozonolysis of 3β,28-di-O-acetyl-29-norlupan-20-one-O-methylketoxime in the presence of ketones was used as an example to show that secondary ozonides at the C20 position of betulin are unstable and decompose to form the “anomalous product” methyl-3β,28-di-O-acetyl-29,30-bisnorlupan-20-oate, the structure of which was proved by an x-ray crystal structure analysis.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1

Similar content being viewed by others

References

  1. K. Griesbaum, Trends Org. Chem., 6, 145 (1997).

    CAS  Google Scholar 

  2. K. Griesbaum, X. Liu, A. Kassiaris, and M. Scherer, Liebigs Ann., 1381 (1997).

  3. G.-J. Ten Brink, I. W. C. E. Arends, and R. A. Sheldon, Chem. Rev., 104, 4105 (2004).

    Article  PubMed  CAS  Google Scholar 

  4. R. T. Aplin, R. P. K. Chan, and T. G. Halsall, J. Chem. Soc. C, 2322 (1969).

  5. P. S. Bailey, Chem. Rev., 58, 925 (1958).

    Article  CAS  Google Scholar 

  6. F. W. Semmler, Ber. Dtsch. Chem. Ges., 42, 246 (1909).

    Article  CAS  Google Scholar 

  7. O. B. Flekhter, G. V. Giniyatullina, F. Z. Galin, N. Zh. Baschenko, N. S. Makara, F. S. Zarudii, E. I. Boreko, O. V. Savinova, N. I. Pavlova, Z. A. Starikova, and G. A. Tolstikov, Khim. Prir. Soedin., 582 (2005).

  8. O. B. Kazakova, N. I. Medvedeva, and K. Yu. Suponitskii, Khim. Prir. Soedin., 365 (2011).

  9. APEX2 and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA, 2005.

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

    Article  Google Scholar 

Download references

Acknowledgment

The work was supported financially by the RFBR (Project No. 09-03-00831) and a grant of the RF President for State Support of Young Russian Scientists (MD-3852.2009.3.).

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 450054, Ufa, Russia

    O. B. Kazakova, E. Yu. Yamansarov, O. S. Kukovinets, N. I. Medvedeva, D. V. Kazakov & O. K. Kornilov

  2. N. A. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

    K. Yu. Suponitskii

Authors
  1. O. B. Kazakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. Yu. Yamansarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. S. Kukovinets
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. I. Medvedeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. V. Kazakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. O. K. Kornilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. K. Yu. Suponitskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. B. Kazakova.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2011, pp. 648–650.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kazakova, O.B., Yamansarov, E.Y., Kukovinets, O.S. et al. Anomalous ozonolysis product of 3β,28-di-O-acetyl-29-norlupan-20-one-O-methyloxime. Chem Nat Compd 47, 738–740 (2011). https://doi.org/10.1007/s10600-011-0047-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-011-0047-6

Keywords

Search

Navigation