Solid phase synthesis of 3-toluenesulfonylglutarimides

Journal of the Chinese Chemical Society

Volumn 50, Issue 4, 2003, Pages 795-797

  Chang, Meng Yang ^a   Lin, Kuo Ging ^b   Chen, Shui Tein ^b   Chang, Nein Chen ^c  

^a NATIONAL UNIVERSITY OF KAOHSIUNG   (Taiwan)

^b INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

^c NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

Glutarimides; Rink Amide resin; Solid phase reaction; Stepwise 3+3 strategy; Thalidomide

Indexed keywords

EID: 2342492679     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200300111     Document Type: Article

References (40)

1. (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
2. (b) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
3. (c) Balkenhohl, F.; von dem Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288.
4. (d) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449.
5. (e) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Ree, D. C. Tetrahedron 1997, 53, 5643.
6. (f) Yli-Kauhaluoma, J. Tetrahedron 2001, 57, 7053.
7. (g) Krchnak, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61.
8. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
9. (a) Moreia, A. L.; Corral, L. G.; Ye, W.; Johnson, B. A.; Stirling, D.; Muller, G. W.; Freedman, V. H.; Kaplan, G. AIDS Res. Hum. Retroviruses 1997, 13, 857.
10. (b) Dawson, N.; Figg, W. D.; Brawley, O. W.; Bergan, R.; Cooper, M. R.; Senderowicz, A.; Headlee, D.; Steinberg, S. M.; Sutherland, M.; Patronas, N.; Sausville, E.; Linehan, W. M.; Reed, E.; Sartor, O. Chin. Cancer Res. 1998, 4, 37.
11. (c) Waelbroeck, M.; Lazareno, S.; Plaff, O.; Friebe, T.; Tastoi, M.; Mutschler, E.; Lambert, G. Br. J. Pharmacol. 1996, 119, 1319.
12. (d) Park, M.; Lee, J.; Choi, J. Bioorg. Med. Chem. Lett. 1996, 6, 1297.
13. (a) Nazar, F.; Pham-Huy, C.; Galons, H. Tetrahedron Lett. 1999, 40, 3697.
14. (b) Leung, C. S.; Rowlands, M. G.; Jarman, M.; Foster, A. B.; Griggs, L. J.; Wilman, D. E. V. J. Med. Chem. 1987, 30, 1550.
15. (c) Knabe, J.; Wahl, S. Arch. Pharm. 1987, 330, 1032.
16. (d) Polonski, T. J. Chem. Soc., Perkin Trans, 1 1988, 639.
17. (e) Kim, M. H.; Patel, D. V. Tetrahedron Lett. 1994, 35, 5603.
18. (f) Robin, S.; Zhu, J.; Galons, H.; Pham-Huy, C.; Claude, J. R.; Tomas, A.; Viossat, B. Tetrahedron Asymm. 1995, 6, 1249.
19. (g) Zhu, J.; Pham-Huy, C.; Lemoine, P.; Tomas, A.; Galons, H. Heterocycles 1996, 43, 1923.
20. (h) Kometani, T.; Fitz, T.; Watt, D. S. Tetrahedron Lett. 1986, 27, 919.
21. (i) Bach, T.; Bergman, H.; Brummerhop, H.; Lewis, W.; Harms, K. Chem. Eur. J. 2001, 7, 4512.
22. (a) Chang, M. Y.; Chang, B. R.; Tai, H. M.; Chang, N. C. Tetrahedron Lett. 2000, 41, 10273.
23. (b) Huang, C. G.; Chang, B. R.; Chang, N. C. Tetrahedron Lett. 2002, 43, 2721.
24. (c) Chang, B. R.; Chen, C. Y.; Chang, N. C. Tetrahedron Lett. 2002, 43, 3233.
25. (d) Chang, M. Y.; Chen, S. T.; Chang, N. C. Tetrahedron 2002, 58, 3623.
26. (e) Chang, M. Y.; Chen, S. T.; Chang, N. C. Tetrahedron 2002, 58, 5075.
27. (f) Hsu, R. T.; Cheng, L. M.; Chang, N. C.; Tai, H. M. J. Org. Chem. 2002, 67, 5044.
28. (g) Chang, M. Y.; Chen, S. T.; Chang, N. C. Heterocycles 2002, 57, 2321.
29. (h) Chang, M. Y.; Lin, J. Y. C.; Chen, S. T.; Chang, N. C. J. Chin. Chem. Soc. 2002, 49, 1015.
30. (i) Chang, M. Y.; Lin, J. Y. C.; Chen, S. T.; Chang, N. C. J. Chin. Chem. Soc. 2002, 49, 1079.
31. (j) Chang, M. Y.; Chen, S. T.; Chang, N. C. Heterocycles 2003, 60, 99.
32. (k) Chang, M. Y.; Chang, C. H.; Chen, S. T.; Chang, N. C. J. Chin. Chem. Soc. 2002, 49, 383.
33. Coste, J.; Dutour, M. N.; Pantaloni, A.; Castro, B. Tetrahedron Lett. 1990, 37, 205.
34. 3): δ 170.84, 164.64, 146.06, 134.74, 130.01 (2×), 129.15 (2×), 64.85, 28.47, 21.80, 18.87.
35. (a) Makonkawkeyoon, S.; Limoson-Probre, R. N. R.; Moreira, A. L.; Schauf, V.; Kaplan, G. Proc. Natl. Acad. Sci. USA 1993, 90, 5974.
36. (b) Amato, R. D. PCT Int Appl WO 940,085
37. (Chem. Abstr., 1995, 122, 151376r).
38. (a) Muller, G. W.; Konnecke, W. E.; Smith, A. M.; Khetani, V. D. Org. Proc. Res. & Devel. 1999, 3, 139.
39. (b) Xiao, Z.; Schaefer, K.; Firestine, S.; Li, P.-K. J. Comb. Chem. 2002, 4, 149.
40. 4: C. 60.47; H, 3.90. Found: C, 60.41; H, 3.86.