A new photocleavable linker in solid-phase chemistry for ether cleavage

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2315-2317

  Glatthar, Ralf ^a   Giese, Bernd ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001614960     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006076h     Document Type: Article

References (51)

1. (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
2. (b) Ellman J. A. Acc. Chem. Res. 1996, 29, 132.
3. (c) Broach, J. R.; Thorner, J. Nature 1996, 384, 14.
4. (d) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1988, 3293.
5. (e) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817.
6. (a) Pillai, V. N. R. Synthesis 1980, 1.
7. (b) Lloyd-Williams, P.; Albericio, F.; Giralt, E. Tetrahedron 1993, 49, 11065.
8. Terret, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51 (30), 8135.
9. (a) Rich, D. H.; Gurwara, S. K. J. Am. Chem. Soc. 1975, 97, 1575. Renil, M.; Pillai, V. N. R. Tetrahedron Lett. 1994, 35, 3809.
10. (a) Rich, D. H.; Gurwara, S. K. J. Am. Chem. Soc. 1975, 97, 1575. Renil, M.; Pillai, V. N. R. Tetrahedron Lett. 1994, 35, 3809.
11. (b) Holmes, C. P. J. Org. Chem. 1997, 62, 2370. Yoo, D. J.; Greenberg, M. M. J. Org. Chem. 1995, 60, 3358.
12. (b) Holmes, C. P. J. Org. Chem. 1997, 62, 2370. Yoo, D. J.; Greenberg, M. M. J. Org. Chem. 1995, 60, 3358.
13. (c) Ajayagosh, A.; Pillai, V. N. R. Tetrahedron 1988, 44, 6661.
14. (d) Ajayagosh, A.; Pillai, V. N. R. J. Org. Chem. 1987, 52, 5714.
15. (e) Wang, S.-S. J. Org. Chem. 1976, 41, 3258. Bellof, D.; Mutter, M. Chimia 1985, 39, 317.
16. (e) Wang, S.-S. J. Org. Chem. 1976, 41, 3258. Bellof, D.; Mutter, M. Chimia 1985, 39, 317.
17. (f) Rock, R. S.; Chan, S. I. J. Org. Chem. 1996, 61, 1526.
18. Peukert, S.; Giese, B. J. Org. Chem. 1998, 63, 9045.
19. For a general review of alcohols achieved by cleavage from a linker, see: (a) James I. W. Tetrahedron 1999, 4855.
20. (b) Guillier, F.; Orain, D.; Bradley M. Chem. Rev. 2000, 100, 2091.
21. (a) Frechet, J. M. J.; Nuygens, L. J. Can. J. Chem. 1976, 54, 926. Krchnak, V. S. W. A. Tetrahedron Lett. 1988, 23, 3023.
22. (a) Frechet, J. M. J.; Nuygens, L. J. Can. J. Chem. 1976, 54, 926. Krchnak, V. S. W. A. Tetrahedron Lett. 1988, 23, 3023.
23. (b) Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427. Wallace, O. B. Tetrahedron Lett. 1997, 38, 4939.
24. (b) Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427. Wallace, O. B. Tetrahedron Lett. 1997, 38, 4939.
25. (c) Deegan, T. L.; Gooding, O. W.; Baudart, S.; Porco, J. A., Jr. Tetrahedron Lett. 1997, 38, 4973.
26. Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733.
27. (d) Garigipati, R. S. Tetrahedron Lett. 1997, 38, 6807.
28. (a) Kurth, M. J.; Randall, L. A. A.; Takenouchi, K. J. Org. Chem. 1996, 61, 8755.
29. (b) Schore, N. E.; Najdi, S. D. J. Am. Chem. Soc. 1990, 112, 441.
30. (c) Berteina, S.; De Mesmaeker, A. Tetrahedron Lett. 1998, 39, 5759.
31. Deegan, T. L.; Gooding, O. W.; Baudart, S.; Porco, J. A., Jr. Tetrahedron Lett. 1997, 38, 4973.
32. (a) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
33. (b) Ley, S. V.; Mynett, D. M.; Koot, W.-J. Synlett 1995, 1017.
34. (c) Tietze, L. F.; Hippe, T.; Steinmetz, A. Chem. Commun. 1998, 793.
35. (a) Hu, Y.; Porco, J. A. J.; Labadie, J. W.; Gooding, O. W. J. Org. Chem. 1998, 63, 4518.
36. (b) Stranix, B. R.; Liu, H. Q.; Darling, G. D. J. Org. Chem. 1997, 62, 6183.
37. (c) Thompson, L. A.; Moore, F. L.; Moon, Y.; Ellman, J. A. J. Org. Chem. 1998, 63, 2066.
38. (d) Chan, T.-H.; Huang, W.-Q. J. Chem. Soc., Chem. Commun. 1985, 909.
39. Alsina, J.; Chiva, C.; Ortiz, M.; Rabanal, F.; Girald, E.; Albericio, F. Tetrahedron Lett. 1997, 38, 883.
40. (a) Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M. J. Org. Chem. 1997, 62, 5660.
41. (b) Dell'Aquita, D.; Imbach, J.-L.; Rayner B. Tetrahedron Lett. 1997, 38, 5289.
42. (c) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449.
43. Beside the epoxidation, dihydroxylation of 7 with subsequent esterification is possible, too. See also ref 5.
44. Adam, W.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
45. Kaiser, E.; Coleacott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595.
46. Fontenot, J. D.; Miller, J. M.; David, M. A.; Montelaro, R. C. Pept. Res. 1991, 4, 19.
47. Oded, A.; Houghten, R. A. Pept. Res. 1990, 3, 42.
48. Look, G. C.; Holmes, C. P.; Chinn, J. P.; Gallop, M. A. J. Org. Chem. 1994, 59, 7588.
49. 0.001-0.01% concentrated HCl in the corresponding solvent (pH ∼5.0-5.5); 0.1 equiv of HCl relative to the ether is sufficient to catalyze this reaction.
50. 3 the photolysis generated small amounts of HCl (pH ∼4.5-5.5).
51. 2. That corresponds to a pH value of 1-2.