Monatshefte für Chemie / Chemical Monthly

, Volume 122, Issue 1–2, pp 101–110 | Cite as

Pheromone, 1. Mitt.: (+)-cis-Disparlure: Synthese und Feldtests

  • Christian R. Noe
  • Max Knollmüller
  • Helmut Kürner
  • Gerhard Steinbauer
  • Helmut Koberg
  • Peter Gärtner
Organische Chemie Und Biochemie

(+)-cis-Disparlure: Synthesis and field tests

Summary

A synthesis of (+)-cis-disparlure is described starting from racemic 2-hydroxy-dodecannitrile (2), which is transformed into the O-protected enantiomerically pure cyanohydrine4. Grignardreaction followed by reduction with BH3 · (CH3)2S yields the correspondingthreo-configurated secondary alcohol10. After tosylation and cleavage of theMBE-protective-group (+)-cis-disparlure (14) is obtained by treatment with KOH. Mating disruption field tests exhibited a significantly increased effectiveness of (+)-cis-disparlure as compared to the racemic product.

Keywords

(+)-cis-Disparlure Enantioselective synthesis Field tests Mating disruption 

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Literatur

  1. [1]
    Plimmer J. R., Leonhardt B., Schwalbe C. P., Webb R. E. (1982) Management of the Gypsy Moth with Its Sex Attractant Pheromone. In: Leonhardt B., Beroza M. (eds.) Insect Pheromone Technology Chemistry and Application (ACS Symposium Series, No. 290). American Chemical Society, Washington, pp. 231–242Google Scholar
  2. [2]
    Iwaki S., Marumo S. (1974) J. Am. Chem. Soc.96: 7842Google Scholar
  3. [3] (a)
    Yamada M., Saito T., Katugiri K., Iwaki S., Marumo S. (1976) J. Insect Physiol.22: 755;Google Scholar
  4. [3] (b)
    Vité J. P., Klimetzek D., Loskant G., Hedden R., Mori K. (1976) Naturwissenschaften63: 582Google Scholar
  5. [3] (c)
    Miller J. R., Roelofs W. L. (1978) Environ. Entomol.7: 42Google Scholar
  6. [4] (a)
    Plimmer J. R., Schwalbe C. P., Paszek E. C., Bierl B. A., Webb R. E., Maumo S., Iwaki S. (1977) Environ. Entomol.6: 518;Google Scholar
  7. [4] (b)
    Miller J. R., Mori K., Roelofs W. L. (1977) J. Insect Physiol.23: 1447Google Scholar
  8. [5]
    Cardé R. T., Doane C. C., Baker T. C., Iwaki S., Marumo S. (1977) Environ. Entomol.6: 768Google Scholar
  9. [6]
    Cardé R. T., Doane C. C., Farnum D. G. (1978) Environ. Entomol.7: 815Google Scholar
  10. [7] (a)
    Beroza M. (1960) Agric. Chem.15: 37;Google Scholar
  11. [7] (b)
    Babson A. L. (1963) Science142: 447;Google Scholar
  12. [7] (c)
    Beroza M., Knipling E. F. (1972) Science177: 19Google Scholar
  13. [8] (a)
    Mori K., Takigawa T., Matsui M. (1976) Tetrahedron Lett.44: 3953;Google Scholar
  14. [8] (b)
    Mori K., Takigawa T., Matsui M. (1979) Tetrahedron35: 833;Google Scholar
  15. [8] (c)
    Achmatowicz O., Sadownik J., Sadownik A. (1985) J. Carbohydr. Chem.4: 435Google Scholar
  16. [9]
    Noe C. R., Knollmüller M., Kürner H., Steinbauer G. (1990) Öst. Pat. 390789 (25.6. 1990) (Prior. 3.11.88; AT 2701/88)Google Scholar
  17. [10]
    Noe C. R., Knollmüller M., Kürner H. (1989) Eur. Pat. 0162235 (18.1. 1989) (Prior. 4.4. 84, AT 1136/84)Google Scholar
  18. [11] (a)
    Cason J. (1942) J. Am. Chem. Soc.64: 1106; darin zitiert: Dreger E. (1932) Org. Synth. Coll. Voll.8: 306;Google Scholar
  19. [11] (b)
    Mori K., Ebata T. (1986) Tetrahedron42: 3471Google Scholar
  20. [12]
    Noe C. R. (1982) Chem. Ber.115: 1591Google Scholar
  21. [13]
    Noe C. R., Knollmüller M., Steinbauer G., Jangg E., Völlenkle H. (1988) Chem. Ber.121: 1231Google Scholar

Copyright information

© Springer-Verlag 1991

Authors and Affiliations

  • Christian R. Noe
    • 1
  • Max Knollmüller
    • 2
  • Helmut Kürner
    • 2
  • Gerhard Steinbauer
    • 3
  • Helmut Koberg
    • 4
  • Peter Gärtner
    • 1
  1. 1.Christian-Doppler-Laboratorium für Chirale Verbindungen: Chemische SyntheseWienÖsterreich
  2. 2.Institut für Organische ChemieTechnische Universität WienWienÖsterreich
  3. 3.Chemie Linz Ges.m.b.H.LinzÖsterreich
  4. 4.Agro Linz Ges.m.b.H.LinzÖsterreich

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