Skip to main content
Log in

Reaction of (+)-usninic acid and several of its derivatives with diazomethane

  • Published:
Chemistry of Natural Compounds Aims and scope

New derivatives of (+)-usninic acid including products of ring expansion, methylation of enol and phenol hydroxyls, and formation of an oxirane ring in addition to products with pyran and furan rings annelated to ring A of (+)-usninic acid were prepared by reaction of (+)-usninic acid and its pyrazole derivatives with diazomethane.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. K. Ingolfsdottir, Phytochemistry, 61, 729 (2002).

    Article  PubMed  CAS  Google Scholar 

  2. V. Galasso, Chem. Phys., 374, 138 (2010).

    Article  CAS  Google Scholar 

  3. J. F. W. McOmie (ed.), Protective Groups in Organic Chemistry, Premium Press, 1973.

  4. L. Bertilsson and C. Wachtmeister, Acta Chem. Scand., 22, 3081 (1968).

    Article  CAS  Google Scholar 

  5. A. J. Pearson and W. R. Roush (eds.), Handbook of Reagents for Organic Synthesis. Activating Agents and Protecting Groups, John Wiley & Sons, 1999.

  6. F. A. Khan, R. Satapathy, S. Sudheer, and C. N. Rao, Tetrahedron Lett., 46, 7193 (2005).

    Article  CAS  Google Scholar 

  7. O. Illa, C. Rodriguez-Garcia, C. Acosta-Silva, I. Favier, D. Picurelli, A. Oliva, M. Gomez, V. Branchadell, and R. M. Ortuno, Organometallics, 26, 3306 (2007).

    Article  CAS  Google Scholar 

  8. K. V. Vatsuro and G. L. Mishchenko, Name Reactions in Organic Chemistry [in Russian], Khimiya, Moscow, 1976.

    Google Scholar 

  9. F. Carey, Organic Chemistry, 5th Ed., McGraw-Hill, 2004.

  10. N. F. Salakhutdinov, M. P. Polovinka, and M. Yu. Panchenko, RF Pat. No. 2,317,076C1; Byull. Izobret., No. 5 (2008).

  11. M. Takai, U. Yoshimasa, and J. A. Beisler, J. Med. Chem., 22, No. 11, 1380 (1979).

    Article  PubMed  CAS  Google Scholar 

  12. Organicum [translated from German], in 2 vol., 2nd Vol., 4th Ed., Mir, Moscow, 2008.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. N. Sokolov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2011, pp. 623–627.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sokolov, D.N., Luzina, O.A., Korchagina, D.V. et al. Reaction of (+)-usninic acid and several of its derivatives with diazomethane. Chem Nat Compd 47, 708–712 (2011). https://doi.org/10.1007/s10600-011-0041-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-011-0041-z

Keywords

Navigation