Synthesis of a CDE fragment of the insect antifeedant 12-hydroxyazadiradione

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9097-9102

  Fernández Mateos, Alfonso ^a   Coca, Gustavo Pascual ^a   González, Rosa Rubio ^a   Hernández, Carolina Tapia ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001350277     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961100j     Document Type: Article

References (30)

1. (a) Taylor, D. A. H. Prog. Chem. Org. Nat. Prod. 1984, 45, 1.
2. (b) Champagne, D. E.; Koul, O.; Isman, M. B.; Scudder, G. G. E.; Towers, G. H. N. Phytochemistry 1992, 31, 377.
3. (a) Mitra, C. R.; Garg, H. S.; Pandy, G. N. Tetrahedron Lett. 1970, 2761.
4. (b) Siddiqui, S.; Siddiqui, B. S.; Faizi, S.; Mahmood, T. J. Nat. Prod. 1988, 51, 30.
5. (c) Reference (1a) pag. 34;
6. (d) Rajab, M. S.; Bentley, M. D.; Fort, R. C., Jr. J. Nat. Prod. 1988, 51, 168.
7. Kraus, W. Biologically active compounds from Meliaceae. In Chemistry and Biotechnology of Biologically Active Natural Products; Proceedings of the Second Internacional Conference; Budapest, 15-19 August, 1983. Szantay, Ca., Ed.; Studies in Organic Chemistry. 17; Elsevier: Amsterdam, 1984; pp 331-345.
8. Gedye, R. N.; Aura, P. C.; Deck, K. Can. J. Chem. 1971, 49, 1764.
9. Kozikowski, A. P.; Li, C.-S. J. Org. Chem. 1987, 52, 3541.
10. Kozikowski, A. P.; Chen, Y.-Y.; Wang, B. C.; Xu, Z.-B. Tetrahedron 1984, 40, 2345.
11. All compounds synthesized are racemic modifications, although only one enantiomer is depicted.
12. Curran, D. P. J. Am. Chem. Soc. 1983, 105, 5826.
13. Eliel, E. L.; Ro, R. S. Stereoselective Reductions; Doyle, M. P., West, Ch. T., Eds.; Dowden, Hutchinson & Ross, Inc.: Pennsylvania, 1976; p 236.
14. (a) Fukuyama, Y.; Kawashima, Y.; Miwa, T.; Tokoroyama, T. Synthesis 1974, 443.
15. (b) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233.
16. (c) Renoud-Grappin, M.; Vanucci, C.; Lhommet, G. J. Org. Chem. 1994, 59, 3902.
17. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
18. (b) Scott, W. J.; Stille, J, K. J. Am. Chem. Soc. 1986, 108, 3033.
19. (c) Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 50, 9583.
20. Pinhey, J. T.; Roche, E. G. J. Chem. Soc., Perkin Trans. 1 1988, 2415.
21. Harnish, W.; Morera, E.; Ortar, G. J. Org. Chem. 1985, 50, 1990.
22. Mc Murry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
23. Barton, D. H. R.; Bashiardes, G.; Fourrey, J. L. Tetrahedron 1988, 44, 147.
24. Mateos, A. F.; de la Fuente, J. A. J. Org. Chem. 1990, 55, 1349.
25. Mateos, A. F.; López, A.; Pascual, G.; Rubio, R.; Tapia, C. Synlett 1995, 409.
26. (a) Coxon, J. M.; Lim, C. E. Aust. J. Chem. 1977, 30, 1137.
27. (b) Blackett, B. N.; Coxon, J. M.; Hartshorn, M. P.; Richards, K. E. Aust. J. Chem. 1970, 23, 2077.
28. (a) Grieco, P. A.; Pogonowski, Ch. S.; Burke, S. J. Org. Chem. 1975, 40, 542.
29. Ronald, R. C.; Lansinger, J. M.; Lillie, T. S.; Wheeler, C. J. J. Org. Chem. 1982, 47, 2451.
30. Baraldi, P. G.; Barco, A.; Benetti, S.; Ferretti, V.; Pollini, G. P.; Polo, E.; Zanirato, V. Tetrahedron 1989, 45, 1517.