Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Reactions affecting the γ-lactone ring of α-santonin

  • 51 Accesses

  • 2 Citations

Abstract

The selective dehydrogenation of the eudesmanolide α-santonin and its alkylation with the introduction of an allyl fragment into its γ-lactone ring are described. It has been established that these reactions are regio- and stereo-selective. The structures of the compounds obtained were determined from their IR, UV, PMR, and mass spectra.

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

Literature cited

  1. 1.

    A. K. Picman, Biochem. Syst. Ecol.,14, No. 3, 255–281 (1986).

  2. 2.

    P. Barbetti and C. G. Casinovi, Ann. Ist. Super. Sanita.,17, 255–281 (1981).

  3. 3.

    A. M. El-Sayed, E. S. A. Aboutabl, and A. A. Elarrouny, Egypt. J. Pharm. Sci.,29, No. 1–4, 43–51 (1988).

  4. 4.

    J. T. Edward and M. J. Davis, J. Org. Chem.,43, No. 4, 536–541 (1978).

  5. 5.

    A. Fronlich, M. P. Imbert, K. Ishikawa, T. B. H. McMurry, and D. Rayne, Proc. Royal Irish Acad.,83, 65–72 (1983).

  6. 6.

    D. J. L. Clive, Tetrahedron,34, No. 8, 1049–1132 (1978).

  7. 7.

    A. G. Gonzalez, J. Bermejo, H. Mansilla, G. M. Massenet, I. Cabrera, J. M. Amaro, and A. Galindo, Phytochemistry,16, 1836–1837 (1977).

  8. 8.

    F. C. Seaman, Bot. Rev.,48, No. 2, 595 (1982).

  9. 9.

    R. G. Kelsey and F. Shafizadeh, Phytochemistry,18, No. 9, 1591–1611 (1979).

  10. 10.

    A. D. Kagarlitskii, S. M. Adekenov, and A. N. Kupriyanov, Sesquiterpene Lactones of the Plants of Central Kazakhstan [in Russian], Nauka, Alma-Ata (1987).

Download references

Additional information

Institute of Organic Synthesis and Coal Chemistry, Kazakhstan Academy of Sciences, Karaganda. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 518–522, September–October, 1992.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Adekenov, S.M., Gafurov, N.M. Reactions affecting the γ-lactone ring of α-santonin. Chem Nat Compd 28, 452–455 (1992). https://doi.org/10.1007/BF00630648

Download citation

Keywords

  • Sesquiterpene Lactone
  • Diselenide
  • Isopropylamine
  • Exomethylene
  • Diphenyl Diselenide