Solid-phase directed ortho-lithiation and the preparation of a phthalide library

Journal of Combinatorial Chemistry

Volumn 3, Issue 4, 2001, Pages 332-340

  Garibay, Patrick ^a   Vedsø, Per ^b   Begtrup, Mikael ^b   Hoeg Jensen, Thomas ^a  

^a NOVO NORDISK A S   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002616195     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc000082n     Document Type: Article

References (62)

1. Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997-10999.
2. (a) Brown, R. C. J. Chem. Soc, Perkin Trans. 1 1998, 3293-3320.
3. (b) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
4. (c) Hermkens, P. H.; Ottenheijm, H. C.; Rees, D. Tetrahedron 1996, 52, 4527-4554.
5. (d) Hermkens, P. H.; Ottenheijm, H. C.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678.
6. (e) Booth, S.; Hermkens, P. H.; Ottenheijm, H. C.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
7. (f) Thompson, L.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
8. Snieckus, V. Chem. Rev. 1990, 90, 879-933.
9. Farrall, M. J.; Frechét, J. M. J. J. Org. Chem. 1976, 41, 3877-3882.
10. Fraley, M. E.; Rubino, R. S. Tetrahedron Lett. 1997, 38, 3365-3368.
11. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1997, 38, 7669-7672.
12. (a) Tietze, L. F.; Steinmetz, A. Synlett 1996, 667-668.
13. (b) Halm, C.; Evarts, J.; Kurth, M. J. Tetrahedron Lett. 1997, 38, 7709-7712.
14. Tempest, P. A.; Armstrong, R. W. J. Am. Chem. Soc. 1997, 119, 7607-7608.
15. Li, Z. G.; Ganesan, A. Synlett 1998, 405-406.
16. Havez, S.; Begtrup, M.; Vedsø, P.; Andersen, K.; Ruhland, T. J. Org. Chem. 1998, 63, 7418-7420.
17. Boehm, T. L.; Showalter, H. D. J. Org. Chem. 1996, 61, 6498-6499.
18. Garibay, P.; Toy, P. H.; Hoeg-Jensen, T.; Janda, K. D. Synlett 1999, 1438-1440.
19. Toy, P. H.; Reger, T. S.; Garibay, P.; Garno, J. C.; Malikayil, J. A.; Liu, G.; Janda, K. D. J. Comb. Chem. 2001, 3, 117-124.
20. Toy, P. H.; Janda, K. D. Tetrahedron Lett. 1999, 40, 6329-6332.
21. Puterbaugh, W. H.; Hauser, C. R. J. Am. Chem. Soc. 1964, 29, 853-856.
22. Beak, P.; Brown, R. A. J. Org. Chem. 1979, 44, 4463-4464.
23. Beak, P.; Brown, R. A. J. Org. Chem. 1982, 47, 34-36.
24. Beak, P.; Tse, A.; Hawkins, J.; Chen, C. W. Tetrahedron 1983, 39, 1983-1989.
25. (a) Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commun. 1998, 39, 297-298.
26. (b) Ahmed, A.; Clayden, J.; Rowley, M. Tetrahedron Lett. 1998, 39, 6103-6106.
27. (c) Ahmed, A.; Clayden, J.; Yasin, S. A. Chem. Commun. 1999, 39, 231-232.
28. Bayer, E. Angew. Chem., Int. Ed. Engl. 1991, 30, 113-129.
29. Meldal, M. Tetrahedron Lett. 1992, 33, 3077-3080.
30. Rademann, J.; Grøtli, M.; Meldal, M.; Bock, K. J. Am. Chem. Soc. 1999, 121, 5459-5466.
31. Malenfant, P. R.; Frechét, J. M. J. Chem. Commun. 1998, 2657-2658.
32. Polytetrahydrofuran cross-linked polystyrene resins (Janda-Jel) are now commercially available from Aldrich.
33. Erase, S.; Dahmen, S. Chem. - Eur. J. 2000, 6, 1899-1905.
34. MacLean, D.; Baldwin, J. J.; Ivanov, V. T.; Kato, Y.; Shaw, A.; Schneider, P.; Gordon, E. M. J. Comb. Chem. 2000, 2, 562-578.
35. Examples of systems where we believe the term "hidden linker" would be appropriate: (a) Fivush, A. M.; Willson, T. M. Tetrahedron Lett. 1997, 38, 7151-7154.
36. (b) Huang, W. L.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668.
37. (c) Blaney, P.; Grigg, R.; Rankovic, Z.; Thoroughgood, M. Tetrahedron Lett. 2000, 41, 6639-6642.
38. (d) Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288-3295.
39. Mao, C. L.; Barnish, I. T.; Hauser, C. R. J. Heterocycl. Chem. 1969, 6, 475-482.
40. Slocum, D. W.; Jennings, C. A. J. Org. Chem. 1976, 41, 3653-3664.
41. Narasimhan, N. S.; Bhide, B. H. Tetrahedron 1971, 27, 6171-6176.
42. Sartori, G.; Bigi, F.; Tao, X. C.; Porta, C.; Maggi, R.; Predieri, G.; Lanfranchi, M.; Pellinghelli, M. A. J. Org. Chem. 1995, 60, 6588-6591.
43. Iwao, M.; Kuraishi, T. Tetrahedron Lett. 1985, 26, 6213-6216.
44. Page, P.; Bradley, M.; Walters, I.; Teague, S. J. Org. Chem. 1999, 64, 794-799.
45. Hirao, A.; Hayashi, M.; Nakahama, S. Macromolecules 1996, 29, 3353-3358.
46. (a) Kienzle, F. Helv. Chim. Acta 1979, 61, 449.
47. (b) Lin, S. T.; Yang, F. M. J. Chem. Res., Synop. 1994, 292-292.
48. (a) Ray, J. K.; Harvey, R. G. J. Org. Chem. 1982, 47, 5-3336.
49. (b) Carissimo-Rietsch, F.; Schmitz, C.; Aubry, J. M. Tetrahedron Lett. 1991, 32, 3845-3846.
50. (a) Marxer, A.; Rodriguez, H. R.; McKenna, J. M.; Tsai, H. M. J. Org. Chem. 1975, 40, 1427-1433.
51. (b) Martin, L. L.; Worm, M.; Agnew, M. N.; Kruse, H.; Wilker, J. C.; Geyer, H. M. J. Med. Chem. 1981, 24, 617-621.
52. (c) Jacobs, S. A.; Cortez, C.; Harvey, R. G. Chem. Commun. 1981, 1215-1216.
53. (d) Harvey, R. G.; Cortez, C.; Jacobs, S. A. J. Org. Chem. 1982, 47, 2120-2125.
54. (e) Ghosh, D.; Snyder, S. E.; Watts, V. J.; Mailman, R. B.; Nichols, D. E. J. Med. Chem. 1996, 39, 549-555.
55. Sibi, M. P.; Miah, M. A.; Snieckus, V. J. Org. Chem. 1984, 49, 737-742.
56. Slocum, D. W.; Reed, D.; Jackson, F.; Friesen, C. J. Organomet. Chem. 1996, 512, 265-267.
57. (a) Rottländer, M.; Boymond, L.; Cahiez, G.; Knochel, P. J. Org. Chem. 1999, 64, 1080-1081.
58. (b) Rottländer, M.; Boymond, L.; Berillon, L.; Lepretre, A.; Varchi, G.; Avolio, S.; Laaziri, W.; Queguiner, G.; Ricci, A.; Cahiez, G.; Knochel, P. Chem. - Eur. J. 2000, 6, 767-770.
59. (c) Boymond, L.; Rottländer, M.; Cahiez, G.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1701-1703.
60. Thompson, L. A.; Ellman, J. A. Tetrahedron Lett. 1994, 35, 9333-9336.
61. Suffert, J. J. Org. Chem. 1989, 54, 509-510.
62. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595-598.