Diels-alder cycloaddition approach to puupehenone-related metabolites: Synthesis of the potent angiogenesis inhibitor 8-epipuupehedione

Journal of Organic Chemistry

Volumn 72, Issue 9, 2007, Pages 3332-3339

  Alvarez Manzaneda, E J ^a   Chahboun, R ^a   Cabrera, E ^a   Alvarez, E ^a   Haidour, A ^a   Ramos, J M ^a   Alvarez Manzaneda, R ^a,b   Hmamouchi, M ^a,c   Bouanou, H ^a,c  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF ALMERÍA   (Spain)

^c MOHAMMED V UNIVERSITY   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

8-EPIPUUPEHEDIONE; ANGIOGENESIS INHIBITORS; DIELS-ALDER CYCLOADDITION;

BIOACTIVITY; CYCLOADDITION; KETONES; SYNTHESIS (CHEMICAL);

METABOLITES;

8 EPIPUUPEHEDIONE; ANGIOGENESIS INHIBITOR; CHROMAZONAROL; OXIDE; POLYPHENOL DERIVATIVE; PUUPEHENONE; SCLAREOL; TERPENOID; UNCLASSIFIED DRUG;

ANGIOGENESIS; ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; METABOLITE;

ANGIOGENESIS INHIBITORS; CHEMISTRY, ORGANIC; SESQUITERPENES; TERPENES; XANTHENES; XANTHONES;

EID: 34247594184     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0626663     Document Type: Article

References (51)

1. For some reviews, including the isolation and biological activity of this type of compound, see: (a) Capon, R. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: New York, 1995; Vol. 15, pp 289-326.
2. (b) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75-125.
3. (c) Sipkema, D.; Fraussen, M. C. R.; Osinga, R.; Tramper, J.; Wijffels, R. H. Mar. Biotechnol. 2005, 7, 142-162.
4. (d) Gross, H.; Konig, G. M. Phytochem. Rev. 2006, 5, 115-141.
5. (a) Kohmoto, S.; McConnell, O. J.; Wright, A.; Koehn, F.; Thompson, W.; Lui, M.; Snader, K. M. J. Nat. Prod. 1987, 50, 336-336.
6. (b) Sova, V.; Fedoreev, S. A. Khim. Prir. Soedin. 1990, 497-500.
7. (c) Longley, R. E.; McConnel, O. J.; Essich, E.; Harmody, D. J. Nat. Prod. 1993, 56, 915-920.
8. (d) Nasu, S. S.; Yeung, B. K. S.; Hamann, M. T.; Scheuer, P. J.; Kelly-Borges, M.; Goins, K. J. Org. Chem. 1995, 60, 7290-7292.
9. (e) El Sayed, K. A.; Dunbar, D. C.; Perry, T. L.; Wilkins, S. P.; Hamann, M. T.; Greenplate, J. T.; Wideman, M. A. J. Agric. Food Chem. 1997, 45, 2735-2739.
10. (f) Faulkner, D. J. Nat. Prod. Rep. 1998, 113-158 and references therein.
11. (g) Bourguet-Kondracki, M. L.; Lacombe, F.; Guyot, M. J. Nat. Prod. 1999, 62, 1304-1305.
12. (h) Popov, A. M.; Stekhova, S. I.; Utkina, N. K.; Rebachuk, N. M. Pharm. Chem. J. 1999, 33, 71-73.
13. (i) El Sayed, K. A.; Bartyzel, P.; Shen, X.; Perry, T. L.; Zjawiony, J. K.; Hamann, M. T. Tetrahedron 2000, 56, 949-953.
14. (j) Takamatsu, S.; Hodges, T. W.; Rajbhandari, I.; Gerwick, H.; Hamann, M. T.; Nagle, D. G. J. Nat. Prod. 2003, 66, 605-608.
15. (k) Pina, I. C.; Sanders, M. L.; Crews, P. J. Nat. Prod. 2003, 66, 2-6.
16. (l) Hamann, M. T. Curr. Pharm. Des. 2003, 9, 879-889.
17. (m) Graus, G. A.; Nguyen, T.; Bae, J.; Hostetter, J. Steadham, E. Tetrahedron 2004, 60, 4223-4225.
18. (a) Castro, M. E.; Gonzalez-Iriarte, M.; Barrero, A. F.; Salvador-Tormo, N.; Muñoz-Chapuli, R.; Medina, M. A.; Quesada, A. R. Int. J. Cancer 2004, 110, 31-38.
19. (b) Amagata, T.; Whitman, S.; Johnson, T. A.; Stessman, C. C.; Loo, C. P.; Lobkovsky, E.; Clardy, J.; Crews, P.; Holman, T. R. J. Nat. Prod. 2003, 6, 230-235.
20. (a) Navi, B. N.; Perzanovski, H. P.; Ross, R. A.; Erdman, T. R.; Scheuer, P. J.; Finar, J.; Clardy, J. Pure Appl. Chem. 1979, 51, 1893-1900.
21. (b) Hamann, M. T.; Scheuer, P. J.; Kelly-Borges, M. J. Org. Chem. 1993, 58, 6565-6569.
22. (c) Urban, S.; Capon, R. J. J. Nat. Prod. 1996, 59, 900-901.
23. (d) Hua, D. H.; Huang, X.; Chen, Y.; Battina, S. K.; Tamura, M.; Noh, S. K.; Koo, S. I.; Namatame, I.; Tomoda, H.; Perchellet, E. M.; Perchellet, J. P. J. Org. Chem. 2004, 69, 6065-6078.
24. Takao, K.- I.; Sasaki, T.; Kozaki, T.; Yaganisawa, Y.; Tadano, K.-I.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294 and references therein.
25. Hamann, M. T.; Scheuer, P. J. Tetrahedron Lett. 1991, 32, 5671-5672.
26. Alvarez-Manzaneda, E. J.; Chahboun, R.; Barranco Pérez, I.; Cabrera, E.; Alvarez, E.; Alvarez-Manzaneda, R. Org. Lett. 2005, 7, 1477-1480.
27. (a) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1975, 31, 1117-1118.
28. (b) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Herrador, M. M.; Chahboun, R.; Galera, P. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328.
29. (c) Villamizar, J.; Plata, F.; Canuda, N.; Tropper, E.; Fuentes, J.; Orcajo, A. Synth. Commun. 2006, 36, 311-320.
30. (a) Roll, D. M.; Manning, J. K.; Carter, G. T. J. Antibiot. 1998, 51, 635-639.
31. (b) Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297-302.
32. (c) Kurdyumov, A. V.; Hsung, R. P. J. Am. Chem. Soc. 2006, 128, 6272-6273.
33. (a) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 8101-8104.
34. (b) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron 1998, 54, 5635-5650.
35. (a) Trammel, G. L. Tetrahedron Lett. 1978, 1525-1528.
36. (b) Ishibashi, H.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc 2004, 126, 11122-11123.
37. (a) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328.
38. (b) Arjona, O.; Garranzo, M.; Maluego, J.; Maroto, E.; Plumet, J.; Sáez, B. Tetrahedron Lett. 1997, 38, 7249-7252.
39. (c) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208.
40. (d) Quideau, S.; Lebon, M.; Lamidey, A.- M. Org. Lett. 2002, 22, 3975-3978.
41. (e) Armstrong, V.; Barrero, A. F.; Alvarez-Manzaneda, E. J.; Cortés, M.; Sepúlveda, B. J. Nat. Prod. 2003, 66, 1382-1383.
42. Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391.
43. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Altarejos, J.; Salido, S.; Ramos, J. M. Tetrahedron 1993, 49, 10405-10412.
44. Aricu, A. N.; Andreeva, I. Y.; Vlad, P. F. Russ. Chem. Bull. 1996, 45, 2645-2648;
45. Izv. Akad. Nauk. Ser. Khim. 1996, 2785-2789;
46. Chem. Abstr. 1997, 127, 157649m.
47. Gao, X.; Matsuo, Y.; Snider, B. B. Org. Lett. 2006, 8, 2123-2126.
48. For a study on the regioselectivity of the Fremy's salt oxidation, see: Deya, P. M.; Dopico, M.; Raso, A. G.; Morey, J.; Saa, J. M. Tetrahedron 1987, 43, 3523-3532.
49. Ahn, J. H.; Cho, S. Y.; Ha, J. D.; Chu, S. Y.; Jung, S. H.; Jung, Y. S.; Baek, J. Y.; Choi, I. K.; Shin, E. Y.; Kang, S. K.; Kim, S. S.; Cheon, H. G.; Yang, S.- D.; Choi, J.- K. Bioorg. Med. Chem. Lett. 2002, 12, 1941-1946.
50. For studies on the mechanism of the benzeneseleninic anhydride oxidation, see: (a) Barton, D. H. R.; Brewster, A. G.; Ley, S. V.; Read, C. M.; Rosenfeld, M. N. J. Chem. Soc., Perkin Trans. 1 1981, 1473-1476.
51. (b) Barton, D. H. R.; Finet, J.- P.; Thomas, M. Tetrahedron 1988, 44, 6397-6406.