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Chemistry of Heterocyclic Compounds

, Volume 52, Issue 10, pp 788–796 | Cite as

Synthetic Transformations of Sesquiterpene Lactones 10*. Synthesis of 13-Arylguaianolides

  • Anarkul S. Kihkentayeva
  • Elvira E. Shults
  • Yurii V. Gatilov
  • Sergey S. Patrushev
  • Sultan Karim
  • Gayane A. Atazhanova
  • Sergazy M. Adekenov
Article
  • 85 Downloads

The Heck reaction of methylidene lactones of guaiane type, arglabin and ludartin, with aryl halides occurs with the formation of the respective (E)- and (Z)-13-arylidene-substituted derivatives and the respective endocyclic isomer, the ratio of which depends on the nature of methylidenelactone and the reaction conditions. The arylation of ludartin occurred with a lower yield of the target products and was accompanied by the formation of chamazulene. The interaction of grosheimin with aryl halides under Heck reaction led to the exocyclic products with (E)- and (Z)-configuration, with the latter as the major isomers. The structure of two compounds was established by X-ray structural analysis.

Keywords

arglabin grosheimin guaianolides ludartin sesquiterpenoids Heck reaction X-ray structural analysis 

Notes

The work was performed with financial support from the Russian Science Foundation (project No. 14-13-00822). The authors gratefully acknowledge the contribution by the Collective Chemical Service Center of Siberian Branch of the Russian Academy of Sciences for the spectral and analytical studies.

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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Anarkul S. Kihkentayeva
    • 1
  • Elvira E. Shults
    • 2
    • 3
  • Yurii V. Gatilov
    • 2
    • 3
  • Sergey S. Patrushev
    • 2
    • 3
  • Sultan Karim
    • 1
  • Gayane A. Atazhanova
    • 1
  • Sergazy M. Adekenov
    • 1
  1. 1.JSC “International Research and Production Holding Phytochemistry”KaragandaRepublic of Kazakhstan
  2. 2.N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of Russian Academy of SciencesNovosibirskRussia
  3. 3.Novosibirsk National Research State UniversityNovosibirskRussia

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