Studies toward frondosin A and its analogues. Formal total synthesis of (±)-frondosin A

Organic Letters

Volumn 10, Issue 15, 2008, Pages 3287-3290

  Li, Xin ^a,b   Keon, Alec E ^a   Sullivan, Jonathan A ^a   Ovaska, Timo V ^a  

^a The Holleran Center for Community Action and Public Policy   (United States)

^b Shanghai Hengrui Pharmaceuticals Co Ltd   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; ETHER DERIVATIVE; FRONDOSIN A;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BICYCLO COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; ETHERS; MOLECULAR STRUCTURE;

EID: 49649084474     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8011343     Document Type: Article

References (38)

1. Patil, A. D.; Freyer, A. J.; Killmer, L.; Offen, P.; Carte, B.; Jurewicz, A. J.; Johnson, R. K. Tetrahedron 1997, 53, 5047.
2. (a) Seitz, M.; Dewald, B.; Gerber, N.; Baggiolini, M. J. Clin. Invest. 1991, 87, 463-469.
3. (b) Miller, E. J.; Cohen, A. B.; Nagao, D.; Griffith, R. J.; Maunder, R. J.; Martin, T. R.; Weiner-Kronish, J. P.; Sticherling, M.; Christophers, E.; Matthay, M. A. Am. Rev. Respir. Dis. 1992, 146, 247.
4. (a) Brat, D. J.; Bellail, A. C.; Van Meir, E. G. Neuro-oncol. 2005, 7, 122.
5. (b) Zhu, Y. M.; Webster, S. J.; Flower, D.; Woll, P. J. Br. J. Cancer 2004, 91, 1970.
6. (c) Yuan, A.; Chen, J. J.; Yao, P. L.; Yang, P. C. Front. Biosci. 2005, 853.
7. Lane, B. R.; Lore, K.; Bock, P. J.; Andersson, J.; Coffey, M. J.; Strieter, R. M.; Markovitz, D. M. J. Virol. 2002, 76, 11570.
8. Lane, B. R.; Lore, K.; Bock, P. J.; Andersson, J.; Coffey, M. J.; Strieter, R. M.; Markovitz, D. M. J. Virol. 2001, 75, 8195.
9. Hallock, Y. F.; Cardellina, J. H., II; Boyd, M. R. Nat. Prod. Lett 1998, 11, 153.
10. Inoue, M.; Carson, M. W.; Frontier, A. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 1878.
11. (a) Hughes, C. C.; Trauner, D. Angew. Chem., Int. Ed. 2002, 41, 1569.
12. (b) Hughes, C. C.; Trauner, D. Tetrahedron 2004, 60, 9675.
13. Kerr, D. J.; Willis, A. C.; Flynn, B. L. Org. Lett. 2004, 6, 457.
14. Li, X.; Ovaska, T. V. Org. Lett. 2007, 9, 3837.
15. Li, X.; Kyne, R. E.; Ovaska, T. V. Tetrahedron 2007, 63, 1899.
16. Trost, B. M.; Hu, Y.; Horne, D. B. J. Am. Chem. Soc. 2007, 129, 11781.
17. (a) Trost, B. M.; Shen, H. C.; Horne, D. B.; Toste, F. D.; Steinmetz, B. G.; Koradin, C. Chem. Eur. J. 2005, 11, 2577.
18. (b) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149.
19. (c) Trost, B. M.; Shen, H. C. Angew. Chem., Int. Ed. 2001, 40, 2313.
20. For an early example of this sequence, see: Marvell, E. N.; Titterington, D. Tetrahedron Lett. 1980, 2123.
21. (a) Ovaska, T. V.; Roark, J. L.; Shoemaker, C. M. Tetrahedron Lett. 1998, 39, 5705.
22. (b) Ovaska, T. V.; Roses, J. B. Org. Lett. 2000, 2, 2361.
23. (c) Ovaska, T. V.; Reisman, S. E.; Flynn, M. A. Org. Lett. 2001, 3, 115.
24. (d) Ovaska, T. V.; Ravi Kumar, J. S.; Hulford, C. A.; O'Sullivan, M. F.; Reisman, S. E. Tetrahedron Lett. 2002, 43, 1939.
25. (e) McIntosh, C. E.; Martinez, I.; Ovaska, T. V. Synlett 2004, 2579.
26. (f) Martinez, I.; Alford, P. E.; Ovaska, T. V. Org. Lett. 2005, 7, 1133.
27. (g) Li, X.; Kyne, R. E.; Ovaska, T. V. Org. Lett. 2006, 8, 5153.
28. (h) Li, X.; Kyne, R. E.; Ovaska, T. V. J. Org. Chem. 2007, 72, 6624.
29. Yan, T.-H.; Tsai, C.-C.; Chien, C.-T.; Cho, C.-C.; Huang, P-C. Org. Lett. 2004, 6, 4961.
30. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
31. For related "deconjugative" processes of enone systems, see e.g.: (a) Rychnovsky, S. D.; Mickus, D. E. J. Org. Chem. 1992, 57, 2732.
32. (b) Rizvi, S. Q. A.; Williams, J. R. J. Org. Chem. 1981, 46, 1127.
33. (c) Malhotra, S. K.; Ringold, H. J. J. Am. Chem. Soc. 1963, 85, 1538.
34. The crystallographic data for compound 12 have been deposited with the Cambridge Crystallographic Data Center (CCDC 687989).
35. Rodilla, J. M. L.; Silva, M. L. A.; Diez, D.; Urones, J. G.; Sanz, F. Tetrahedron Asymmetry 2004, 15, 1793.
36. For representative examples of Pd catalyzed α-arylation of ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
37. (b) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360.
38. (c) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.