A convergent and highly efficient synthesis of (E,Z)-2,13-octadecadienyl acetate and (E,Z)-3,13-octadecadienyl acetate, components of the sex pheromone of the Leopard Moth Zeuzera pyrina, through sulfones

Organic Letters

Volumn 1, Issue 6, 1999, Pages 845-848

  Capdevila, Anna ^b   Prasad, Attaluri R ^a,b   Quero, Carmen ^b   Petschen, Inés ^b   Bosch, Maria P ^b   Guerrero, Angel ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004104835     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990114j     Document Type: Article

References (28)

1. (1) Tonini, C.; Cassani, G.; Massardo, P.; Guglielmetti, G.; Castellari, P. L. J. Chem. Ecol. 1986, 12, 1545.
2. Malosse, C.; Descoins, C.; Frérot, B. J. High Resolut. Chromatogr. 1993, 16, 123.
3. Quero, C. Ph.D. Thesis, University of Barcelona, 1996.
4. (a) Tumlinson, J. H.; Yonce, C. E.; Doolittle, C. E.; Heath, R. R.; Gentry, C. R.; Mitchell, E. R. Science 1974, 185, 614.
5. (b) Priesner, E.; Dobler, G.; Voerman, S. Ent. Exp. Appl. 1986, 41, 313.
6. Voerman, S.; Persoons, C. J.; Priesner, E. J. Chem. Ecol. 1984, 10, 1371.
7. Shwarz, M.; Klun, J. A.; Leonhardt, B. A.; Johnson, D. T. Tetrahedron Lett. 1983, 24, 1007.
8. Hoskovec, M.; Saman, D.; Koutek, B. Collect. Czech. Chem. Commun. 1990, 55, 2270.
9. Sharma, M. L.; Thapar, S.; Gupta, R. Ind. J. Chem. 1990, 29B, 657.
10. Uchida, M.; Nakagawa, K.; Mori, K. Agric. Biol. Chem. 1979, 43, 1919.
11. Abrams, S. R.; Nucciarone, D. D.; Steck, W. F. Can. J. Chem. 1983, 61, 1073.
12. Gardette, M.; Alexakis, A.; Normant, J. F. J. Chem. Ecol. 1983, 9, 225.
13. Ramiandrasoa, F.; Descoins, C. Synth. Commun. 1989, 19, 2703.
14. Moiseenkov, A. M.; Czeskis, B. A.; Ivanova, N. M.; Nefedov, O. M. J. Chem. Soc., Perkin Trans. 1 1991, 2639.
15. Ohloff, G.; Vial, C.; Näf, F.; Pawlak, M. Helv. Chim. Acta 1977, 60.
16. Ducoux, J. P.; Le Ménez, P.; Kunesch, N.; Wenkert, E. Tetrahedron 1992, 48, 6403.
17. Camps, F.; Gasol, V.; Guerrero, A. Synthesis 1987, 511.
18. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 23, 2117.
19. Achyatha Rao, S.; Knochel, P. J. Org. Chem. 1991, 56, 4591.
20. For a review, see: Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon Press: Oxford, 1993; Vol. 10.
21. Olson, G. L.; Cheung, H.-C.; Morgan, K. D.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3287.
22. Manescalchi, F.; Orena, M.; Savoia, D. Synthesis 1979, 445.
23. Feixas, J.; Capdevila, A.; Camps, F.; Guerrero, A. J. Chem. Soc., Chem. Commun. 1992, 1451.
24. Feixas, J.; Capdevila, A.; Guerrero, A. Tetrahedron 1994, 50, 8539.
25. Pine, S. H.; Shen, G.; Bautista, J.; Sutton, C., Jr.; Yamada, W.; Apodaca, L. J. Org. Chem. 1990, 55, 2234.
26. When the reaction was carried out at -78°C, the ketone resulting from oxidative desulfonylation of 14 was also obtained, as determined by its spectral properties. equation presented
27. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477.
28. 2: C, 77.87; H, 11.78. Found: C, 77.88; H, 11.90.