Synthetic studies towards the clerodane insect antifeedant jodrellin A: Preparation of a polycyclic model compound with antifeedant activity

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 7, 1996, Pages 611-620

  Cuñat, Ana C ^a   Díez Martín, David ^b   Ley, Steven V ^a   Montgomery, Francis J ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345197102     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960000611     Document Type: Article

References (36)

1. (a) S. V. Ley, in Recent Advances in the Chemistry of Insect Control II; ed. by L. Crombie, Royal Society of Chemistry, Cambridge, 1990, p. 90-98;
2. (b) Ae. de Groot, B. J. M. Jansen, H. J. Swarts, A. A. Verstegen-Haaksma and C. T. Bouwman, in Advances in the Chemistry of Insect Control III, ed. by G. G. Briggs, Royal Society of Chemistry, Cambridge, 1994, p. 195-207.
3. (a) W. M. Blaney, M. S. J. Simmonds, S. V. Ley and P. S. Jones, Entomol. Exp. Appl., 1988, 46, 267;
4. (b) S. V. Ley, J. C. Anderson, W. M. Blaney, E. D. Morgan, R. N. Sheppard, M. S. J. Simmonds, A. M. Z. Slawin, S. C. Smith, D. J. Williams and A. Wood, Tetrahedron, 1991, 47, 9231;
5. (c) W. M. Blaney, M. S. J. Simmonds, S. V. Ley, J. C. Anderson and P. L. Toogood, Entomol. Exp. Appl., 1990, 55, 149;
6. (d) W. M. Blaney, M. S. J. Simmonds, S. V. Ley, J. C. Anderson, S. C. Smith and A. Wood, Pestic. Sci., 1994, 40, 169;
7. (e) M. S. J. Simmonds, W. M. Blaney, S. V. Ley, G. Savona, M. Bruno and B. Rodríguez, Photochemistry, 1989, 28, 1069;
8. (f) P. S. Jones, S. V. Ley, N. S. Simpkins and A. J. Whittle, Tetrahedron, 1986, 42, 6534;
9. (g) A. A. Denholm, L. Jennens, S. V. Ley and A. Wood, Tetrahedron, 1995, 51, 6591.
10. (a) B. Rodriguez, M. C. De la Torre, B. Rodriguez, M. Bruno, F. Piozzi, G. Savona, M. S. J. Simmonds, W. M. Blaney and A. Perales, Phytochemistry, 1993, 33, 309;
11. (b) M. C. De la Torre, M. Bruno, F. Piozzi, B. Rodriguez, G. Savona and O. Servettaz, Phytochemistry, 1992, 31, 3639;
12. (c) M. D. Cole, J. A. Anderson, W. M. Blaney, L. E. Fellows, S. V. Ley, R. N. Sheppard and M. S. J. Simmonds, Phytochemistry, 1990, 29, 1793;
13. (d) P. I. Bozov, P. Y. Malakov, G. Y. Paparov, M. C. De la Torre, B. Rodriguez and A. Perales, Phytochemistry, 1993, 34, 453;
14. (e) H. Bouchard, P. Y. Renard and J. Y. Lallemand, Tetrahedron Lett., 1991, 32, 5953.
15. J. C. Anderson, W. M. Blaney, M. D. Cole, L. L. Fellows, S. V. Ley, R. N. Sheppard and M. S. J. Simmonds, Tetrahedron Lett., 1989, 30, 4737.
16. For a preliminary communication see: W. M. Blaney, A. C. Cuñat, S. V. Ley, F. J. Montgomery and M. S. J. Simmonds, Tetrahedron Lett., 1994, 35, 4861.
17. (a) W. P. Jackson, S. V. Ley and J. A. Morton, Tetrahedron Lett., 1981, 22, 2601;
18. (b) W. P. Jackson, S. V. Ley and J. A. Morton, J. Chem. Soc., Chem. Commun., 1980, 1028;
19. (c) W. P. Jackson, S. V. Ley and J. A. Morton, J. Chem. Soc., Chem. Commun., 1980, 1173.
20. F. J. Montgomery, PhD Thesis, Cambridge University, 1994.
21. T. Mukhopadhgay and D. Seebach, Helv. Chim. Acta, 1982, 385.
22. (a) E. J. Corey, H. Niwa and J. Knolle, J. Am. Chem. Soc., 1978, 100, 1942;
23. (b) R. F. Borch, A. J. Evans and J. J. Wale, J. Am. Chem. Soc., 1977, 99, 1612.
24. J. Herscovici, M.-J. Egron and K. Antonakis, J. Chem. Soc., Perkin Trans. 1, 1982, 1967.
25. M. T. Reetz and B. Wenderoth, Tetrahedron Lett., 1982, 23, 5259 and references cited therein.
26. (a) For a recent review concerning the synthesis and synthetic applications of β-keto esters see: S. Benetti, R. Romagnoli, C. De Risi, G. Spalluto and V. Zanirato, Chem. Rev., 1995, 95, 1065;
27. (b) M. A. Dombroski and B. B. Snider, Tetrahedron, 1992, 48, 1417;
28. (c) B. B. Snider and J. E. Merritt, Tetrahedron, 1991, 47, 8663;
29. (d) C. P. Jasaperse, D. P. Curran and T. L. Levig, Chem. Rev., 1991, 91, 1237.
30. (a) K. B. Sharpless and R. F. Luer, J. Am. Chem. Soc., 1973, 95, 2697;
31. (b) F. A. Davis, O. D. Stringer and J. M. Billmers, Tetrahedron Lett., 1983, 24, 1213;
32. (c) T. Hiroi and K. B. Sharpless, J. Org. Chem., 1978, 43, 1698.
33. P. J. Jones, S. V. Ley, N. S. Simpkins and A. J. Whittle, Tetrahedron, 1986, 42, 6519.
34. (a) M. Rowley and Y. Kishi, Tetrahedron Lett., 1988, 29, 4909;
35. (b) T. Itoh, K. Jitsukawa, K. Kaneda and S. Teranishi, J. Am. Chem. Soc., 1979, 101, 159.
36. L. A. Paquette, R. J. Ross and J. P. Springer, J. Am. Chem. Soc., 1988, 110, 6192.