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Naturwissenschaften

, Volume 67, Issue 3, pp 144–145 | Cite as

Alkaloidal venom mace: Offensive use by a thief ant

  • M. S. Blum
  • T. H. Jones
  • B. Hölldobler
  • H. M. Fales
  • T. Jaouni
Kurze Originalmitteilungen

References

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    Hölldobler, K.: Biol. Zbl.48, 129 (1928)Google Scholar
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    Hölldobler, B.: Oecologia11, 371 (1973)Google Scholar
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    An LKB-9000 combined gas chromatograph-mass spectrometer equipped with a 1.8-m glass column of 3% OV-17 on Supelcoport 80–100 (Supelco, Bellefonte, PA) was used. The column was programmed from 55 °C at 10 °C/min.Google Scholar
  4. 4.
    Pedder, D.J., et al.: Tetrahedron32, 2275 (1976)Google Scholar
  5. 5.
    2-Butyl-5-heptylpyrrolidine was initially synthesized by the cyclization of the N-chloramine utilizing the method described in [4] except that N-chlorosuccinimide was employed to prepare the N-chloramine (Ruschig, H., et al.: Chem. Ber.88, 883 (1955)) instead of NaOClGoogle Scholar
  6. 6.
    2-Butyl-5-heptylpyrrolidine was prepared in the following manner via the 1,4-diketone: Octanal was treated with vinyl magnesium bromide, and the resulting alcohol was oxidized to 1-decen-3-one which was condensed with valeraldehyde (Stetter, H., Kuhlmann, H.: Tetrahedron Lett.1974, 4505). The resulting 5,8-pentadecadione was cyclized to the pyrrole (Young, D.M., Allen, C.H.F.: Org. Syn. Coll.2, 219 (1943)) which was hydrogenated to 2-butyl-5-heptylpyrrolidine. The pyrrolidine and its precursors gave satisfactory elemental analyses and IR, NMR, and mass spectra. The known course of pyrrole hydrogenation favors formation of thecis isomer of the pyrrolidine; GC analysis demonstrated that the final product consisted of a 85/15 ratio of thecis/trans isomer of 2-butyl-5-heptylpyrrolidine. Each isomer was isolated by preparative gas chromatographyGoogle Scholar
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    Jones, T.H., Blum, M.S., Fales, H.M.: Tetrahedron Lett.1979, 1031Google Scholar
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    Ritter, F.J., Persoons, C.J.: Neth. J. Zool.25, 261 (1975)Google Scholar

Copyright information

© Springer-Verlag 1980

Authors and Affiliations

  • M. S. Blum
    • 1
  • T. H. Jones
    • 1
  • B. Hölldobler
    • 2
  • H. M. Fales
    • 3
  • T. Jaouni
    • 3
  1. 1.Department of EntomologyUniversity of GeorgiaAthensUSA
  2. 2.Museum of Comparative ZoologyHarvard UniversityCambridgeUSA
  3. 3.Laboratory of ChemistryNational Heart, Lung and Blood InstituteBethesdaUSA

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