A solution- and solid-phase approach to tetrahydroquinoline-derived polycyclics having a 10-membered ring

Journal of Combinatorial Chemistry

Volumn 6, Issue 5, 2004, Pages 724-734

  Khadem, Shahriar ^a,b   Joseph, Reni ^b   Rastegar, Majid ^b   Leek, Donald M ^b   Oudatchin, Kostantin A ^b   Arya, Prabhat ^a,b  

^a UNIVERSITY OF OTTAWA   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON; QUINOLINE DERIVATIVE;

ARTICLE; ENANTIOSELECTIVITY; RING CLOSING METATHESIS; SOLID; SYNTHESIS;

EID: 4944243450     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049941o     Document Type: Article

References (36)

1. (a) Breimbaur, R.; Vetter, I. R.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 2878-2890.
2. (b) Hinterding, K.; Alonso-Diaz, D.; Waldmann, H. Angew. Chem., Int. Ed. 1998, 37, 688-749.
3. (c) Meseguer, B.; Alonso-Díaz, D.; Griebenow, N.; Herget, T.; Waldmann, H. Angew. Chem., Int. Ed. 1999, 38, 2902-2906.
4. (d) Boger, D. L.; Desharnais, J.; Capps, K. Angew. Chem., Int. Ed. 2003, 42, 4138-4176.
5. (a) Huwe, A.; Mazitschek, R.; Giannis, A. Angew. Chem., Int. Ed. 2003, 42, 2122-2138.
6. (b) Klabunde, T.; Hessler, G. ChemBioChem 2002, 3, 928-944.
7. (c) Peterson, J. R.; Mitchison, T. J. Chem., Biol. 2002, 9, 1275-1285.
8. (a) Berg, T. Angew. Chem., Int. Ed. 2003, 42, 2462-2481.
9. (b) Schreiber, S. L. Bioorg. Med. Chem. 1998, 6, 1127-1152.
10. (c) Crews, C. M.; Mohan, R. Curr. Opin. Chem. Biol. 2000, 4, 47-53.
11. (d) Crews, C. M.; Splittgerber, U. TIBS 1999, 24, 317-320.
12. (e) Stockwell, B. R. TIBTECH 2000, 18, 449-455.
13. (f) Stockwell, B. R. Nat. Rev. Genet. 2000, 1, 116-125.
14. (g) Mayer, T. U. Trends Cell Biol. 2003, 13, 270-277.
15. (a) Schreiber, S. L. Chem. Eng. News 2003, March 3, 51-61.
16. (b) Gura, T. Nature 2000, 407, 282-284.
17. (c) Strausberg, R. L.; Schreiber S. L. Science 2003, 300, 294-295.
18. (d) Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science 2003, 302, 613-618.
19. Dewick P. M. In Medicinal Natural Products- A Biosynthetic Approach; Wiley-Interscience: New York, 2002; Chapter 6.
20. For a review on natural products-based and solution- and solid-phase synthesis leading to the library generation, see: (a) Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150. (b) Wessjohann, L. A. Curr. Opin. Chem. Biol. 2000, 4, 303-309. (c) Weber, L. Curr. Opin. Chem. Biol. 2000, 4, 295-302. (d) Arya, P.; Joseph, R.; Chou, D. T. H. Chem. Biol. 2002, 9, 145-156.
21. For a review on natural products-based and solution- and solid-phase synthesis leading to the library generation, see: (a) Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150. (b) Wessjohann, L. A. Curr. Opin. Chem. Biol. 2000, 4, 303-309. (c) Weber, L. Curr. Opin. Chem. Biol. 2000, 4, 295-302. (d) Arya, P.; Joseph, R.; Chou, D. T. H. Chem. Biol. 2002, 9, 145-156.
22. For a review on natural products-based and solution- and solid-phase synthesis leading to the library generation, see: (a) Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150. (b) Wessjohann, L. A. Curr. Opin. Chem. Biol. 2000, 4, 303-309. (c) Weber, L. Curr. Opin. Chem. Biol. 2000, 4, 295-302. (d) Arya, P.; Joseph, R.; Chou, D. T. H. Chem. Biol. 2002, 9, 145-156.
23. For a review on natural products-based and solution- and solid-phase synthesis leading to the library generation, see: (a) Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150. (b) Wessjohann, L. A. Curr. Opin. Chem. Biol. 2000, 4, 303-309. (c) Weber, L. Curr. Opin. Chem. Biol. 2000, 4, 295-302. (d) Arya, P.; Joseph, R.; Chou, D. T. H. Chem. Biol. 2002, 9, 145-156.
24. (a) Spring, D. R.; Krishnan, S.; Schreiber, S. L. J. Am. Chem. Soc. 2000, 122, 5656-5657.
25. (b) Lee, D. S.; Sello, J. K.; Schreiber S. L. J. Am. Chem. Soc. 1999, 121, 10648-10649.
26. (c) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363.
27. (a) Bieraugel, H.; Jansen, T. P.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673-2674.
28. (b) Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677-680.
29. (c) Schuster, M.; Pernerstorfer, J.; Blechert, S. Angew. Chem., Int. Ed., Engl. 1996, 35, 1979-1980.
30. (d) Yet, L. Chem. Rev. 2000, 100, 2963-3007.
31. (e) Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131-9166.
32. (f) Nubbemeyer, U. Top. Curr. Chem. 2001, 216, 125-196.
33. (g) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-90.
34. Costa, P. R. R.; Torres. L. B.; Rabi, J. A. Ann. Acad. Braz. Cienc. 1980, 52, 483-488.
35. 2 - 0.090 (14 543 reflections total, 6357 unique, 5930 > 2σ). (a) Sheldrick, G. M. SHELXTL, version 6.10; Brucker AXS Inc.: Madison, WI, 2000. (b) Sheldrick, G. M. SADABS, version 2.03; University of Gottingen, Germany, 2002.
36. 2 - 0.090 (14 543 reflections total, 6357 unique, 5930 > 2σ). (a) Sheldrick, G. M. SHELXTL, version 6.10; Brucker AXS Inc.: Madison, WI, 2000. (b) Sheldrick, G. M. SADABS, version 2.03; University of Gottingen, Germany, 2002.