A triple diene-transmissive Diels-Alder strategy to build the quassinoid framework

Organic Letters

Volumn 7, Issue 25, 2005, Pages 5601-5604

  Dion, Amélie ^a   Dubé, Pascal ^a   Spino, Claude ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; QUASSINOID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

CYCLIZATION; FURANS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; QUASSINS;

EID: 29444440364     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0522236     Document Type: Article

References (34)

1. For a review on the isolation and biological activities of quassinoids, see: (a) Guo, Z.; Vangapandu, S.; Sindelar, R. W.; Walker, L. A.; Sindelar R. D. Curr. Med. Chem. 2005, 12, 173-190.
2. (b) Okano, M.; Fukamiya, N.; Lee K. H. Stud. Nat. Prod. Chem. 1990, 7 (pt. A), 369-404.
3. Polonsky, J. Fortschr. Chem. Org. Naturst. 1973, 30, 101-150.
4. (d) Polonsky, J. Fortschr. Chem. Org. Naturst. 1985, 47, 221-264.
5. For a review on the synthesis of quassinoids, see: (a) Kawada, K.; Ki, M.; Watt, D. S. Org. Prep. Proc. Int. 1989, 21, 521-618.
6. (b) Murae, T.; Sasaki M. Stud. Nat. Prod. Chem. 1992, 11, 71-111.
7. For selected syntheses see: (a) Walker, D. P.; Grieco, P. A. J. Am. Chem. Soc. 1999, 121, 9891-9892.
8. (b) Grieco, P. A.; Collins, J. L.; Huffman J. C. J. Org. Chem. 1998, 63, 9576-9579.
9. (c) Shing, T. K. M.; Jiang, Q. J. Org. Chem. 2000, 65, 7059-7069.
10. (d) Hirota, M.; Yokoyama, A.; Miyaji, K.; Nakamura, H.; Takahashi, T. Tetrahedron Lett. 1987, 28, 435-438.
11. (e) Stojanac, H.; Valenta, Z. Can. J. Chem. 1991, 69, 853-855.
12. (f) Kim, M.; Kawada, K.; Gross, R. S.; Watt, D. S. J. Org. Chem. 1990, 55, 504-511.
13. (g) Shing, T. K. M.; Jiang, Q.; Mak, T. C. W. J. Org. Chem. 1998, 63, 2056-2057.
14. (h) VanderRoest, J. M.; Grieco, P. A. J. Org. Chem. 1996, 61, 5316-5325.
15. (i) Hirota, H.; Yokoyama, A.; Miyaji, K.; Nakamura, T.; Igarashi, M.; Takahashi, T. J. Org. Chem. 1991, 56, 1119-1127.
16. (j) Kim, M.; Kawada, K.; Gross, R. S.; Watt, D. S. J. Org. Chem. 1990, 55, 504-511.
17. For a relay synthesis see: (k) Sasaki, M.; Murae, T.; Takahashi, T. J. Org. Chem. 1990, 55, 528-540.
18. (a) Valenta, Z.; Gray, A. H.; Papadopoulos, S.; Podesva, C. Tetrahedron Lett. 1960, 1, 25-33.
19. (b) Valenta, Z.; Gray, A. H.; Orr, D. E.; Papadopoulos, S.; Podesva, C. Tetrahedron 1962, 18, 1433-1441.
20. Cuendet, M.; Pezzuto, J. M. J. Nat. Prod. 2004, 67, 269-272.
21. (a) Spino, C.; Hill, B.; Dubé, P.; Gingras, S. Can. J. Chem 2003, 81, 81-108.
22. (b) Spino, C.; Liu, G.; Tu, N.; Girard, S. J. Org. Chem. 1994, 59, 5596-5608.
23. α-Chloroketones have been prepared in nonracemic form by the alkylation of chiral α-chloro imidates and offers the possibility of an asymmetric version of our synthesis. See: (a) Pridgen, L. N.; De Brosse, C. J. Org. Chem. 1997, 62, 216-220.
24. (b) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39-42.
25. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191-1223.
26. N2′ cuprate displacements, see: (a) Yamanaka, M.; Kato, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 6287-6293.
27. (b) Karlstrom, A.; Sofia, E.; Bäckvall, J.-E. Chem. Eur. J. 2001, 7, 1981-1989.
28. For selected examples involving alkylnyl epoxides, see: (c) Dieter, R. K.; Chen, N.; Yu, H.; Nice, L. E.; Gore, V. K. J. Org. Chem. 2005, 70, 2109-2119.
29. (d) Fernández de la Pradilla, R.; Viso, A.; Castro, S.; Fernández, J.; Manzano, P.; Tortosa, M. Tetrahedron 2004, 60, 8171-8180.
30. Ma, S.; Yu, F.; Gao, W. J. Org. Chem. 2003, 68, 5943-5949.
31. Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552-6554.
32. Dubé, P. Ph.D. Thesis, Université de Sherbrooke, 2005.
33. Spino, C.; Thibault, C.; Gingras, S. J. Org. Chem. 1998, 63, 5283-5287.
34. More, J. D.; Finney, N. S. Org. Lett. 2002, 4, 3001-3003.