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Selective Oxidation of Triterpene Alcohols by Sodium Hypochlorite

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Abstract

3-Oxo-triterpenoids were prepared by oxidation of the methyl esters of glycyrrhetic acid, allobetulin, and 20-oxo-29-nor-betulin with sodium hypochlorite in acetic acid or methylene chloride under phase-transfer conditions.

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REFERENCES

  1. G. A. Lee and H. H. Freedman, Tetrahedron Lett., 17, 1641 (1976).

    Google Scholar 

  2. R. V. Stevens, K. T. Chapman, and H. N. Weller, J. Org. Chem., 45, 2030 (1980).

    Google Scholar 

  3. G. A. Mirafzal and A. M. Lozeva, Tetrahedron Lett., 39, 7263 (1998).

    Google Scholar 

  4. F. J. Moreno-Dorado, F. M. Guerra, F. L. Manzano, F. J. Aladro, Z. D. Jorge, and G. M. Massanet, Tetrahedron Lett., 44, 6691 (2003).

    Google Scholar 

  5. T. Honda, B. V. Rounds, L. Bore, F. G. Favaloro, G. W. Gribble, N. Suh, Y. Wang, and M. B. Sporn, Bioorg. Med. Chem. Lett., 9, 3429 (1999).

    Google Scholar 

  6. D. S. H. L. Kim, Z. Chem, N. Van Nquen, J. M. Pezzuto, S. Quit, and Z.-Z. Lu, Synth. Commun., 27, 1607 (1997).

    Google Scholar 

  7. M. Tori, R. Maisuda, M. Sono, Y. Kohama, and Y. Asakawa, Bull. Chem. Soc. Jpn., 61, 2103 (1988).

    Google Scholar 

  8. O. B. Flekhter, O. Yu. Ashavina, E. I. Boreko, L. T. Karachurina, N. I. Pavlova, N. N. Kaballnova, O. V. Savinova, F. Z. Galin, S. N. Nikolaeva, F. S. Zarudii, L. A. Baltina, and G. A. Tolstikov, Khim.-Farm. Zh., No. 6, 21 (2002).

    Google Scholar 

  9. J. Sejbal, J. Klinot, M. Budesinsky, and J. Protiva, Collect. Czech. Chem. Commun., 62, 1905 (1997).

    Google Scholar 

  10. R. V. Stevens, K. T. Chapman, C. A. Stubbs, W. W. Tam, and K. F. Albizati, Tetrahedron Lett., 23, 4647 (1982).

    Google Scholar 

  11. B. Jursic, Synthesis, 868 (1988).

  12. F. A. Macias, A. M. Simonet, and M. D. Esteban, Phytochemistry, 36, 1369 (1994).

    Google Scholar 

  13. L. A. Baltina, O. B. Flekhter, Zh. M. Putieva, R. M. Kondratenko, L. V. Krasnova, and G. A. Tolstikov, Khim.-Farm. Zh., No. 4, 47 (1996).

    Google Scholar 

  14. T.-S. Li, J.-X. Wang, and X.-J. Zheng, J. Chem. Soc., Perkin Trans. I, 3957 (1998).

  15. L. F. Tolstikova and G. A. Tolstikov, Izv. Akad. Nauk Kaz. SSR, Ser. Khim., 21, 65 (1971).

    Google Scholar 

  16. F. N. Lugemwa, F.-Y. Huang, M. D. Bentley, M. J. Mendel, and A. R. Alford, J. Agric. Food Chem., 493 (1990).

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Flekhter, O.B., Ashavina, O.Y., Smirnova, I.E. et al. Selective Oxidation of Triterpene Alcohols by Sodium Hypochlorite. Chemistry of Natural Compounds 40, 141–143 (2004). https://doi.org/10.1023/B:CONC.0000033930.76751.b7

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  • DOI: https://doi.org/10.1023/B:CONC.0000033930.76751.b7

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