Skip to main content
SpringerLink
Log in

Synthesis of O-Vinyl Ethers of Pentacyclic Triterpene Alcohols and Lupane-Type Oximes

  • Published:
Chemistry of Natural Compounds Aims and scope

Vinylation by acetylene of lupane-type pentacyclic triterpene C-28- and C-3β-alcohols and C-20-oximes in superbase solutions synthesized the corresponding C-28- and C-3β-O-vinyl ethers and C-20-O-vinyloximes. The reaction of 3β,28-dimethoxy-29-norlupan-20-one with acetylene in superbase KOH–DMSO produced a derivative with an N-vinylpyrrole ring in the C-19 side chain.

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

Similar content being viewed by others

References

  1. B. A. Trofimov and N. K. Gusarova, Russ. Chem. Rev., 76 (6), 507 (2007).

    Article  CAS  Google Scholar 

  2. V. V. Voronin, M. S. Ledovskaya, A. S. Bogachenkov, K. S. Rodygin, and V. P. Ananikov, Molecules, 23, 2442 (2018).

    Article  Google Scholar 

  3. M. S. Ledovskaya, V. V. Voronin, and K. S. Rodygin, Russ. Chem. Rev., 87 (2), 167 (2018).

    Article  CAS  Google Scholar 

  4. S. Sugihara, Y. Kawamoto, Y. Maeda, Macromolecules, 49 (5), 1563 (2016).

    Article  CAS  Google Scholar 

  5. B. A. Trofimov and E. Yu. Schmidt, Acc. Chem. Res., 51, 1117 (2018).

    Article  CAS  Google Scholar 

  6. S. Samanta, D. R. Bogdanowicz, H. H. Lu, and J. T. Koberstein, Macromolecules, 49 (5), 1858 (2016).

    Article  CAS  Google Scholar 

  7. A. V. Orlov, N. G. Komissarova, and O. V. Shitikova, Chem. Sustainable Develop., 2, 213 (2011).

    Google Scholar 

  8. A. V. Orlov, N. G. Komissarova, O. V. Shitikova, L. V. Spirikhin, and M. S. Yunusov, Russ. Chem. Bull., 62 (3), 687 (2013).

    Article  CAS  Google Scholar 

  9. K. Hata, K. Hori, and S. Takahashi, J. Nat. Prod., 65, 645 (2002).

    Article  CAS  Google Scholar 

  10. M. S. Yunusov, N. G. Komissarova, and N. G. Belenkova, RU Pat. 2,270,202, Feb. 20, 2006, Byull., No. 5, 2006.

  11. A. M. Vasil’tsov, E. Yu. Schmidt, A. I. Mikhaleva, A. V. Afonin, and A. B. Zaitsev, Chem. Heterocycl. Compd., 37 (12), 1488 (2001).

    Article  Google Scholar 

  12. K. Hiroya, T. Takahashi, N. Miura, A. Naganuma, and T. Sakamoto, Bioorg. Med. Chem., 10, 3229 (2002).

    Article  CAS  Google Scholar 

  13. V. Pouzar and A. Vystrcil, Collect. Czech. Chem. Commun., 41, 3452 (1976).

    Article  CAS  Google Scholar 

  14. J. Kunot, N. Hovorkova, and A. Vystrcil, Collect. Czech. Chem. Commun., 35, 1105 (1970).

    Article  Google Scholar 

  15. M. Kahnt, L. Heller, A. Al-Harrasi, R. Schafer, R. Kluge, C. Wagner, C. Otgonbayar, and R. Csuk, Med. Chem. Res., 27, 1757 (2018).

    Article  CAS  Google Scholar 

  16. 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, Chem. Nat. Compd., 41, 706 (2005).

    Article  CAS  Google Scholar 

  17. A. Vystrcil, V. Krecek, M. Budesinsky, and J. Protiva, Collect. Czech. Chem. Commun., 51, 581 (1986).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The work was performed on a State Task Topic for UfIC, UFRC, RAS (No. AAAA-A17-117011910025-6). The spectral part of the study used equipment at the Khimiya CUC, UfIC, RAS and Agidel RCUC, UfIC, RAS.

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 71 Prosp. Oktyabrya, Ufa, 450054, Russia

    N. G. Komissarova, A. V. Orlov & O. V. Shitikova

Authors
  1. N. G. Komissarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Orlov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Shitikova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. G. Komissarova.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2020, pp. 414–418.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Komissarova, N.G., Orlov, A.V. & Shitikova, O.V. Synthesis of O-Vinyl Ethers of Pentacyclic Triterpene Alcohols and Lupane-Type Oximes. Chem Nat Compd 56, 481–486 (2020). https://doi.org/10.1007/s10600-020-03067-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-020-03067-2

Keywords

Search

Navigation