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Synthesis of lupane and 19β,28-epoxy-18α-oleanane 2,3-seco-derivatives based on betulin

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Chemistry of Natural Compounds Aims and scope

The α-hydroxyoximes of methyl betulonate and allobetulone were synthesized. Beckmann fragmentation of them produced the lupane and 19β,28-epoxy-18α-oleanane 2,3-seco-derivatives.

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References

  1. P. A. Krasutsky, Nat. Prod. Rep., 6, No. 23, 919 (2006).

    Article  Google Scholar 

  2. O. B. Flekhter, L. R. Nigmatullina, L. A. Baltina, L. T. Karachurina, F. Z. Galin, F. S. Zarudii, G. A. Tolstikov, E. I. Boreko, N. I. Pavlova, S. N. Nikolaeva, and O. V. Savinova, Khim.-farm. Zh., No. 9, 26 (2002).

  3. R. Csuk, K. Schmuck, and R. Schafer, Synth. Commun., 27, No. 9, 1607 (1997).

    Article  Google Scholar 

  4. A. Pichette, H. Liu, C. Roy, S. Tanguay, F. Simard, and S. Lavoie, Synth. Commun., 34, No. 21, 3925 (2004).

    Article  CAS  Google Scholar 

  5. T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, O. B. Flekhter, Bioorg. Khim., 32, 42 (2006) [T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, and O. B. Flekhter, Russ. J. Bioorg. Chem., 32, 37 (2006)].

    PubMed  CAS  Google Scholar 

  6. T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, and O. B. Flekhter, Bioorg. Khim., 32, 300 (2006) [T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, and O. B. Flekhter, Russ. J. Bioorg. Chem., 32, 261 (2006)].

    Google Scholar 

  7. M. Urban, J. Sarek, J. Klinot, G. Korinkova, and M. Hajduch, J. Nat. Prod., 67, 1100 (2004).

    Article  PubMed  CAS  Google Scholar 

  8. D. Miljkovic and J. Petrovic, J. Org. Chem., 42, No. 12, 2101 (1977).

    Article  PubMed  CAS  Google Scholar 

  9. V. M. Pejanovic, J. A. Petrovic, J. J. Csanadi, S. M. Stankovic, and D. A. Miljkovic, Tetrahedron, 51, No. 48, 13379 (1995).

    Article  CAS  Google Scholar 

  10. A. Magyar, B. Schonecker, J. Wolfling, G. Schneider, W. Gunther, and H. Gorls, Tetrahedron: Asymmetry, 14, 2705 (2003).

    Article  CAS  Google Scholar 

  11. M. Fieser and L. F. Fieser, Reagents for Organic Synthesis, John Wiley & Sons, New York (1974).

    Google Scholar 

  12. L. F. Tietze and T. Eicher, Preparative Organic Chemistry [translated from Ger.], Mir, Moscow (1999).

  13. B. Keil, Laboratoriumstechnik der organische Chemie, Akademie-Verlag, Berlin (1961).

  14. H. Schulze and H. Pieron, Ber., II, 2332 (1922).

    Google Scholar 

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Acknowledgment

The work was supported financially by the RFBR Grant No. 08-03-00265a.

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Correspondence to V. V. Grishko.

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Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 491–494, September-October, 2008. Original article submitted July 4, 2008.

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Tolmacheva, I.A., Nazarov, A.V., Maiorova, O.A. et al. Synthesis of lupane and 19β,28-epoxy-18α-oleanane 2,3-seco-derivatives based on betulin. Chem Nat Compd 44, 606–611 (2008). https://doi.org/10.1007/s10600-008-9135-7

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  • DOI: https://doi.org/10.1007/s10600-008-9135-7

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