Asymmetric synthesis of both enantiomers of α,α difluoroeldanolide: An interesting property of their biological activity

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 4071-4074

  Itoh, Toshiyuki ^a   Sakabe, Kohei ^a   Kudo, Kazutoshi ^a   Zagatti, Pierre ^b   Renou, Michel ^b  

^a OKAYAMA UNIVERSITY   (Japan)

^b CEMAGREF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA,ALPHA DIFLUOROELDANOLIDE; PHEROMONE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CYCLIZATION; DOSE RESPONSE; OPTICAL ROTATION; RECEPTOR BINDING; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032482489     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00661-3     Document Type: Article

References (24)

1. 1. Welch, J. T. Tetrahedron, 1987, 43, 3123.
2. 2. Itoh, T.; Ohara H.; Emoto, S. Tetrahedron Lett. 1995, 36, 3531.
3. 3. (a) Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron Lett. 1982, 23, 5051.
4. (b) Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron, 1984, 40, 3521.
5. 4. Synthesis of optically active eldanolide via radical cyclization methodology has been reported: Yadav, J. S.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1989, 1824.
6. 5. For some syntheses of optically active synthesis of eldanolide. (a) Angert, H.; Czerwonka, R.; Reißig, H-U. Liebigs Ann. 1996, 259.
7. (b) Paulsen, H.; Hoppe, D. Tetrahedron, 1992, 48, 5667.
8. (c) Sukuki, Y.; Mori, W.; Ishizaki, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931.
9. (d) Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810.
10. (e)Uematsu, T.; Uemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 587. and references cited therein.
11. 6. For an example of EAG experiment for insect pheromones see. Lucas, P.; Renou, M.; Tellier, F.; Hammoud, A.; Audemard, H.; Descoins, C. J. Chem. Ecol. 1994, 20, 489.
12. 7. Reuter, J. M.; Salomon, R. G. J. Org. Chem. 1977, 42, 3360.
13. 8. Dauben, W. G.; Cogen, J. M.; Ganzer, G. A.; Behar, V. J. Am. Chem. Soc. 1991, 113, 5817.
14. 9. Chen, C. -S.; Fujimoto, Y.; Girdauskas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 102, 7294; Chen, C-S.; Wu, S-H.; Girdauskas, G.; Sih, C. J. J. Am. Chem. Soc. 1987, 109, 2812.
15. 9. Chen, C. -S.; Fujimoto, Y.; Girdauskas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 102, 7294; Chen, C-S.; Wu, S-H.; Girdauskas, G.; Sih, C. J. J. Am. Chem. Soc. 1987, 109, 2812.
16. 10. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564; Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741.
17. 10. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564; Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741.
18. 11. Prestwich, G. D. ; Sun, W. C. ; Mayer, M. S. ; Dickens, J. C. J. Chem. Ecol. 1990, 16, 1761. Ding, Y.-S ; Prestwich, G. D. J. Chem. Ecol. 1988, 14, 2033. Prestwich, G. D. ; Streinz, L. J. Chem. Ecol. 1988, 14, 1003.
19. 11. Prestwich, G. D. ; Sun, W. C. ; Mayer, M. S. ; Dickens, J. C. J. Chem. Ecol. 1990, 16, 1761. Ding, Y.-S ; Prestwich, G. D. J. Chem. Ecol. 1988, 14, 2033. Prestwich, G. D. ; Streinz, L. J. Chem. Ecol. 1988, 14, 1003.
20. 11. Prestwich, G. D. ; Sun, W. C. ; Mayer, M. S. ; Dickens, J. C. J. Chem. Ecol. 1990, 16, 1761. Ding, Y.-S ; Prestwich, G. D. J. Chem. Ecol. 1988, 14, 2033. Prestwich, G. D. ; Streinz, L. J. Chem. Ecol. 1988, 14, 1003.
21. Riba, M. ; Eizaguirre, M. ; Sans, A. ; Quero, C. ; Guerrero, A. Pestic. Sci., 1994, 41, 91.
22. 12. Graham, S. M. ; Prestwich, G. D. J. Org. Chem. 1994, 59, 2957; Duran, I.; Parilla, A. ; Feixas, J.; Guerrero, A. Bioorg. Med. Chem. Lett. 1993, 3, 2953. Rosell, G; Herrero, S.; Guerrero, A. Biochem. Biophys. Res. Commun. 1996, 226, 227.
23. 12. Graham, S. M. ; Prestwich, G. D. J. Org. Chem. 1994, 59, 2957; Duran, I.; Parilla, A. ; Feixas, J.; Guerrero, A. Bioorg. Med. Chem. Lett. 1993, 3, 2953. Rosell, G; Herrero, S.; Guerrero, A. Biochem. Biophys. Res. Commun. 1996, 226, 227.
24. 12. Graham, S. M. ; Prestwich, G. D. J. Org. Chem. 1994, 59, 2957; Duran, I.; Parilla, A. ; Feixas, J.; Guerrero, A. Bioorg. Med. Chem. Lett. 1993, 3, 2953. Rosell, G; Herrero, S.; Guerrero, A. Biochem. Biophys. Res. Commun. 1996, 226, 227.