Synthesis of active antifeedant CDE fragments of 11- ketoepoxyazadiradione based on an electrocyclization reaction catalyzed by perchloric acid

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9440-9447

  Fernández Mateos, Alfonso ^a   Martín De La Nava, Eva M ^a   Coca, Gustavo Pascual ^a   González, Rosa Rubio ^a   Ramos Silvo, Ana I ^a   Simmonds, M S J ^b   Blaney, W M ^c  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b JODRELL LABORATORY   (United Kingdom)

^c UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

11 KETOEPOXYAZADIRADIONE; EPOXIDE; INSECTICIDE; KETONE; LIMONOID; PERCHLORIC ACID; UNCLASSIFIED DRUG;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; EPOXIDATION; LEPIDOPTERA; PEST CONTROL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 0032509283     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981456q     Document Type: Article

References (20)

1. (a) Fernández-Mateos, A.; de la Fuente, J. A. J. Org. Chem. 1990, 55, 1349.
2. (b) de la Fuente, J. A.; Marugán, J. J.; Cross, S. S.; Fernández-Mateos, A.; García, S.; Menéndez, A. Bioorg. Med. Chem. Lett. 1995, 14, 1471.
3. (c) Champagne, D. E.; Koul, O.; Isman, M. B.; Scudder, G. G. E.; Towers, G. H. N. Phytochemistry 1992, 31, 377.
4. (a) Fernández-Mateos, A.; López Barba, A. J. Org. Chem. 1995, 60, 3580.
5. (b) Fernández-Mateos, A.; Pascual Coca, G.; Rubio González, R.; Tapia Hernández, C. Tetrahedron 1996, 52, 4817.
6. (c) Fernández-Mateos, A.; López Barba, A.; Pascual Coca, G.; Rubio González, R.; Tapia Hernández, C. Synthesis 1997, 1381.
7. (d) Fernández-Mateos, A.; Pascual Coca, G.; Pérez Alonso, J. J.; Rubio González, R.; Tapia Hernández, C. Synlett 1997, 1134.
8. Rubinstein, M. J. Org. Chem. 1962, 27, 3886.
9. Akiyama, S.; Nakatsuji, S.; Hamamura, T. Tetrahedron Lett. 1979, 20, 2809.
10. (a) Santelli-Rouvier, C.; Santelli, M. Synlett 1983, 429.
11. (b) Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. 1994, 45, 1.
12. All compounds synthesized are racemic modifications, although only one enantiomer is depicted.
13. Edwards, B. E., Rao, P. N. J. Org. Chem. 1966, 31, 324.
14. McMurry, J. E.; Musser, J. H.; Ahmad, M. S.; Blaszczak, L. C. J. Org. Chem. 1975, 40, 1829.
15. 7a.
16. Fernández-Mateos, A.; López Barba, A.; Martín de la Nava, E.; Pascual Coca, G.; Peréz Alonso, J. J.; Ramos Silvo, A. I.; Rubio González, R. Tetrahedron 1997, 53, 14131.
17. 6 axial, respectively.
18. 13C correlation experiments and were found to be in complete agreement with the proposed structures and stereochemistries.
19. Kraus, W.; Cramer, R. Tetrahedron Lett. 1978, 21, 2395.
20. Blaney, W. M.; Simmonds, M. S. J.; Ley, S. V.; Anderson, J. C.; Toogood, P. L. Entomol. Exp. Appl. 1990, 55, 149.