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Chemistry of Heterocyclic Compounds

, Volume 48, Issue 2, pp 384–385 | Cite as

Formation of a novel heterocyclic system based on natural alantolactone

  • S. G. KlochkovEmail author
  • S. V. Afanasˈeva
  • S. A. Pukhov
Article
Natural sesquiterpene lactones which contain an exocyclic methylene group in the β-position of the lactone ring react readily with N-nucleophiles to give compounds having novel forms of biological activity when compared with the starting compounds [ 1]. When the reaction was carried out with 5α-epoxyalantolactone ( 1) (a secondary metabolite of the plant genus Inula L. [ 2]) and the tryptamine derivatives 2a,b we were able to show the formation of the novel heterocyclic system, namely the hydrogenated benzo[ g]furo[4,3,2- cd]indolones 3a,b.

Keywords

epoxyalantolactone 9a-hydroxy-1-[2-(1 H-indol-3-yl)ethyl]-5a,9-dimethyldodecahydro-benzo[g]furo[4,3,2-cd]indol-3(1 H)-ones tryptamines Michael reaction 

References

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    N. J. Lawrence, A. T. McGown, J. Nduka, J. A. Hadfield, and R. G. Pritchard, Bioorg. Med. Chem. Lett., 11, 429 (2001).CrossRefGoogle Scholar
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    T. Konishi, Y. Shimada, T. Nagao, H. Okabe, and T. Konoshima, Biol. Pharm. Bull., 25, 1370 (2002).CrossRefGoogle Scholar
  3. 3.
    S. G. Klochkov, S. V. Afanas'eva, and A. N. Pushin, Khim. Prirod. Soedin., 325 (2006). [Chem. Nat. Compd., 42, 400 (2006)].Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • S. G. Klochkov
    • 1
    Email author
  • S. V. Afanasˈeva
    • 1
  • S. A. Pukhov
    • 1
  1. 1.Institute of Physiologically Active CompoundsChernogolovkaRussia

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