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Terpenoids.Cis-trans- andtrans-cis- Nepetalactones

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Zusammenfassung

Die beiden stereoisomeren Nepetalactone wurden durch Gaschromatographie getrennt. Es wurde gezeigt, dass dastrans-cis-Isomere (II) auf Katzen anziehend wirkt. Dascis-trans-Isomere (I), das etwa 75% der Mischung darstellt, ist bedeutend weniger aktiv, möglicherweise völlig inaktiv.

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References

  1. S. M. McElvain, P. M. Walters, andR. D. Bright, J. Amer. chem. Soc.64, 1828 (1942).

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  2. R. B. Bates, E. J. Eissenbraun, andS. M. McElvain, J. Amer. chem. Soc.80, 3420 (1958), and references cited therein.

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  3. For nepetalactones distilled from oil of catnip, [α] 23D -13.0° (CHCl3) has been reported, and for nepetalactones from the pyrolysis of nepetalic acid, +3.6° (S. M. McElvain, R. D. Bright, andP. R. Johnson, J. Amer. chem. Soc.63, 1558 (1941)). These preparations probably contained small amounts of a strongly levorotatory impurity.

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  5. The authors gratefully acknowledge financial support from the U.S. Public Health Service (GM-07689).

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, University of Illinois, Urbana, U.S.A.

    R. B. Bates & C. W. Sigel

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  1. R. B. Bates
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  2. C. W. Sigel
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Terpenoids VIII.

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Bates, R.B., Sigel, C.W. Terpenoids.Cis-trans- andtrans-cis- Nepetalactones. Experientia 19, 564–565 (1963). https://doi.org/10.1007/BF02150988

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