Isolation, structural assignment, and synthesis of N-(2-methyl-3- oxodecanoyl)-2-pyrroline, a new natural product from Penicillium brevicompactum with in vivo anti-juvenile hormone activity

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8530-8535

  Moya, Pilar ^a   Cantín, Ángel ^a   Castillo, Maria Angeles ^a   Primo, Jaime ^a   Miranda, Miguel A ^a   Primo Yúfera, Eduardo ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 HEPTYL 3 METHYL 4 OXO 6,7,8,8A TETRAHYDRO 4H PYRROLO[2,1 B] 1,3 OXAZINE; BREVIOXIME; FUNGICIDE; INSECTICIDE; METHANOL; METHYL IODIDE; N (2 METHYL 3 OXODECANOYL) 2 PYRROLINE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HORMONE ACTION; INSECT; METAMORPHOSIS; OXIDATION; STRUCTURE ACTIVITY RELATION;

EID: 0032514971     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972267v     Document Type: Article

References (42)

1. Richardson, M. L., Ed. Chemistry, Agriculture and Environment; The Royal Society of Chemistry: Cambridge, 1991.
2. Pillmoor, J. B.; Wright, K; Terry, A. S. Pestic. Sci. 1993, 39, 131-140.
3. Omura, S. J. Ind. Microbiol. 1992, 10, 135-156.
4. Porter, N.; Fox, F. M. Pestic. Sci. 1993, 39, 161-168.
5. Wright, V. F.; Vesonder, R. F.; Ceigler, A. In Microbial and Viral Pesticides; Kurstak, E., Ed.; Marcel Dekker, Inc.: New York, 1982; pp 559-587.
6. Birkinshaw, J. F.; Raistrick, H.; Ross, D. J. Biochem. J. 1952, 50, 630-634.
7. Oxford, A. E.; Raistrick, H. Biochem. J. 1932, 27, 1902-1906.
8. Oxford, A. E.; Raistrick, H. Biochem. J. 1933, 27, 634-652.
9. Godin, P. Biochim. Biophys. Acta 1955, 11, 114-118.
10. McCorkindale, N. J.; Calzadilla, C. H.; Hutchinson, S. A.; Kitson, D. H.; Ferguson, G.; Campbell, I. M. Tetrahedron 1981, 37, 649-653.
11. Doerfler, D. L.; Bird, B. A.; Campbell, I. M. Phytochemistry 1981, 20, 2303-2304.
12. McCorkindale, N. J.; Baxter, R. L. Tetrahedron 1981, 37, 1795-1801.
13. Ayer, W. A.; Altena, I. V.; Browne, L. M. Phytochemistry 1990, 29 (5), 1661-1665.
14. Birch, A. J.; Wright, J. J. Tetrahedron 1970, 26, 2329-2344.
15. Birch, A. J.; Russell, F. A. Tetrahedron 1972, 28, 2999-3002.
16. Brown, A. G.; Smale, T. C.; King, T. J.; Kasenkamp, R.; Thompson, R. H. J. Chem. Soc., Perkin Trans. 1 1976, 1165-1170.
17. Monger, D. J.; Lim, W. A.; Kerdy, F. J.; Law, J. H. Biochem. Biophys. Res. Commun. 1982, 105, 1374-1380.
18. Hiruma, K.; Yagi, S.; Endo, A. Appl. Entomol. Zool. 1983, 18, 111-115.
19. Edwards, J. P.; Price, N. R. Insect Biochem. Mol. Biol. 1983, 13, 185.
20. Bellés, X.; Camps, F.; Casas, J.; Lloria, J.; Messeguer, A.; Piulachis, M. D.; Sanchez, F. J. Pestic. Biochem. Physiol. 1988, 32, 1-10.
21. Moya, P.; Castillo, M.; Primo-Yúfera, E.; Couillaud, F.; Martínez-Máñez, R.; Garcerá, M. D.; Miranda, M. A.; Primo, J.; Martínez-Pardo, R. J. Org. Chem. 1997, 62, 8544-8545.
22. Bowers, W. S.; Ohta, T.; Cleere, J. S.; Marsella, P. A. Science 1976, 193, 542-547.
23. Oikawa, Y.; Sugano, K.; Yonemitsu, O. J. Org. Chem. 1978, 43, 2087-2088.
24. Oikawa, Y.; Yoshioka, T.; Sugano, K.; Yonemitsu, O. Org. Synth. 1984, 62, 198.
25. Meldrum, A. N. J. Chem. Soc. 1908, 93, 598-601.
26. Davidson, D.; Bernhardt, S. A. J. Am. Chem. Soc. 1948, 70, 3426.
27. Pak, C. S.; Yang, H. C.; Choi, E. B. Synthesis 1992, 1213-1214.
28. Benetti, S.; Romagnoli, R. Chem. Rev. 1995, 95, 1065-1114.
29. Abad, A.; Agulló, C.; Arnó, M.; Cantín, A.; Cuñat, A. C.; Meseguer, B.; Zaragozá, R. J. J. Chem. Soc., Perkin Trans. 1 1997, 1837-1843.
30. Shono, T. Tetrahedron Lett. 1984, 40, 811-850.
31. Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697-6703.
32. Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y. Tetrahedron Lett. 1982, 23, 1201-1204.
33. Shono, T.; Hamaguchi, H.; Matsumura, Y. J. Am. Chem. Soc. 1975, 97, 4262-4268.
34. Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176.
35. Shono, T.; Matsumura, Y.; Tsubata, K. Tetrahedron Lett. 1981, 22, 2411-2412.
36. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
37. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6889-6992.
38. Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. J. Am. Chem. Soc. 1995, 117, 909-917.
39. Moeller, K. D.; Rutledge L. D. J. Org. Chem. 1992, 57, 6360-6363.
40. Moeller, K. D.; Hanau, C. E.; Avignon, A. Tetrahedron Lett. 1994, 35, 825-828.
41. Bowers, W. S. Discovery of Insect Antiallatotropins in The Juvenile Hormones; Gilbert, L. I., Ed. Plenum Press: New York, London, 1976.
42. Staal, G. B. Annu. Rev. Entomol. 1986, 31, 391-429.