Advertisement

Chemistry of Natural Compounds

, Volume 41, Issue 4, pp 420–422 | Cite as

Formation of an Unusual Guaiane Ketopentaenolide from Dehydroisoleucomisin by the Action of Anhydrous DMF and HCl

  • N. A. Talzhanov
  • V. A. Raldugin
  • M. M. Shakirov
  • G. A. Atazhanova
  • S. M. Adekenov
Article

Abstract

Dehydroisoleucomisin (anhydroaustricin) was converted in good yield to guai-1(10),3,5,7(11), 8-pentaen-2-on-12,8-olide by the action of anhydrous HCl in dry DMF. The chemical structure of the product was established using spectral data. The probable formation scheme of this lactone was proposed to include a series of prototopic transformations and ionic dehydrogenation of intermediates.

Key words

dehydroisoleucomisin (anhydroaustricin) DMF HCl guai-1(10),3,5,7(11),8-pentaen-2-on-12,8-olide NMR spectra 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1.
    Y. Amate, J. L. Breton, A.-G. Granados, A. Martinez, M. E. Onorato, and A. S. de Buruaga, Tetrahedron, 46, 6939 (1990).CrossRefGoogle Scholar
  2. 2.
    O. A. Konovalova, K. S. Rybalko, V. I. Sheichenko, and D. A. Pakali, Khim. Prir. Soedin., 741 (1971).Google Scholar
  3. 3.
    I. M. Saitbaeva, A. Mallabaev, and G. P. Sidyakin, Khim. Prir. Soedin., 391 (1983).Google Scholar
  4. 4.
    A. B. Plutno, I. D. Sham'yanov, M. I. Aizikov, M. R. Prokhorova, G. G. Galust'yan, and A. G. Kurmukov, Khim. Prir. Soedin., 687 (1995).Google Scholar
  5. 5.
    N. A. Talzhanov, V. I. Yamovoi, A. T. Kulyyasov, K. M. Turdybekov, and S. M. Adekenov, Khim. Prir. Soedin., 111 (2004).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • N. A. Talzhanov
    • 1
  • V. A. Raldugin
    • 2
  • M. M. Shakirov
    • 2
  • G. A. Atazhanova
    • 1
  • S. M. Adekenov
    • 1
  1. 1.Institute of PhytochemistryMinistry of Education and Science, Republic of KazakhstanKaragandaKazakhstan
  2. 2.N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia

Personalised recommendations