Chemistry of Natural Compounds

, Volume 41, Issue 4, pp 420–422

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

DOI: 10.1007/s10600-005-0167-y

Cite this article as:
Talzhanov, N.A., Raldugin, V.A., Shakirov, M.M. et al. Chem Nat Compd (2005) 41: 420. doi:10.1007/s10600-005-0167-y

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 

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

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