Fluorous synthesis of substituted sclerotigenin library

Journal of Combinatorial Chemistry

Volumn 12, Issue 1, 2010, Pages 125-128

  Lu, Yimin ^a   Nagashima, Tadamichi ^a   Miriyala, Bruhaspathv ^a   Conde, Joanne ^a   Zhang, Wei ^a,b  

^a Fluorous Technologies Inc   (United States)

^b UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPINE DERIVATIVE; FLUORINE; SCLEROTIGENIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; SYNTHESIS;

BENZODIAZEPINONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; FLUORINE; MOLECULAR STRUCTURE;

EID: 74049106526     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9001636     Document Type: Article

References (41)

1. (a) Penhoat, M.; Bohn, P.; Dupas, G.; Papamicael, C.; Marsais, F.; Levacher, V. Tetrahedron.- Asvmmetrv 2006, 17, 281-286.
2. (b) Liu, J. F.; Kaselj, M.; Isome, Y.; Chapnick, J.; Zhang, B.; Bi, G.; Yohannes, D.; Yu, L.; Baldino, C M. J., Org. Chem. 2005, 70, 10488-10493.
3. (c) Grieder, A.; Thomas, A. W. Synthesis 2003,1707-1711.
4. (d) Snider, B. B.; Busuyek, M. V. Tetrahedron 2001, 57, 3301-3307.
5. (e) He, F.; Foxman, B. M.; Snider, B. B. J. Am. Chem. Soc. 1998, 120, 6417-6418.
6. (a) Rahbaek, L.; Breinholt, J. J. Nat, Prod, .1999, 62, 904-905.
7. (b) Sun, H. H.; Barrow, C. J.; Sedlock, D. M.; Gillum, A. M.; Cooper, R. J. Antibiot (Tokyo) 1994, 47, 515-522
8. (c) Goetz, M. A.; Lopez, M.; Monaghan, R. L.; Chang, R. S.; Lotti, V. J.; Chen, T. B.J. Antibiot (Tokyo) 1985, 38, 1633-1637.
9. (a) Sun, H. H.; Barrow, C. J.; Sedlock, D. M.; Gillum, A. M.; Cooper, R. J. Antibiot. 1994, 47, 515-522.
10. (b) Sugimori, T.; Okawa, T.; Eguchi, S.; Kakehi, A.; Yashima, E.; Okamoto, Y. Tetrahedron 1998, 54, 7997-8008.
11. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930.
12. Selected reviews on fluorous synthesis, (a) Zhang, W. Chem. Rev. 2009, 109, 749-795.
13. (b) Curran, D. P. Aldrichemica Acta 2006, 39, 3-9.
14. (c) Curran, D. P. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004; pp 101-127;
15. (d) Zhang, W. Chem, Rev. 2004, 104, 2531-2556.
16. (e) Zhang, W. Curr. Opin. Drue Discov. Develop. 2004, 7, 784-797.
17. (f) Zhang, W. Tetrahedron 2003, 59, 4475-4489.
18. (g) Curran, D. P. Angew. Chem., Int, Ed. 1998, 37, 1174-11.96.
19. Fluorous linker-assisted library synthesis: (a) Werner, S.; Nielsen, S. D.; Wipf, P.; Turner, D. M.; Chambers, P. G.; Geib, S. J.; Curran, D. P.; Zhang, W. J. Comb. Chem. 2009, 11, 452-459.
20. (b) Zhou, H.; Liu, A.; Li, X.; Ma, X.; Feng, W.; Zhang, W.; Yan, B. J. Comb. Chem. 2008, 10, 303-312.
21. (c) Lin, M. J.; Zhang, W.; Sun, C.-M. J. Comb. Chem. 2007, 9, 951-958.
22. (d) Zhang, W.; Lu, Y.; Chen, C. H.-T.; Zeng, L.; Kassel, D. B. J., Comb . Chem. 2006, 8, 687-695.
23. (f) Zhang, W.; Chen, C. H.-T. Tetrahedron Lett. 2005, 46, 1807-1810.
24. (g) Lu, Y.; Zhang, W. Mol. Diversity 2005, 9, 91-98.
25. (h) Nagashima, T.; Zhang, W. J. Comb. Chem. 2004, 6, 942-949.
26. (i) Lu, Y.; Zhang, W. OSAR Comb. Sci. 2004, 23, 827835.
27. (j) Zhang, W.; Tempest, P. Tetrahedron Lett- 2004, 45, 6757-6760.
28. (k) Zhang, W.; Luo, Z.; Chen, C. H.-T.; Curran, D. P. J., Am. Chem. Soc. 2002, 124, 10443-10450.
29. (a) Zhou, H.; Zhang, W.; Yan, B.J. Comb. Chem. in press.
30. (b) Liu, A.; Zhou, H.; Su, G.; Zhang, W.; Yan, B. J. Comb. Chem. 2009, 11, 1083-1093.
31. (c) Zhang, W.; Williams, J. P.; Lu, Y.; Nagashima, T.; Chu, Q. Tetrahedron Lett. 2007, 48, 563-565.
32. (d) Zhang, W.; Lu, Y.; Chen, C. H.-T.; Curran, D. P.; Geib, S. Eur.J. Org. Chem. 2006, 2055-2059.
33. For reviews on F-SPE, see: (a) Zhang, W.; Curran, D. P. Tetrahedron 2006, 62. 11837-11865.
34. (b) Curran. D. P. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004; pp 101-127;
35. (c) Curran, D. P. Synlett 2001, 1488-1496
36. For parallel and automatic F-SPE, see: (a) Zhang, W.; Lu, Y. J. Comb. Chem. 2007, 9, 836-843.
37. (b) Zhang, W.; Lu, Y. J. Comb. Chem. 2006, 8, 890-896.
38. (c) Zhang, W.; Lu, Y.; Nagashima, T. J. Comb. Chem. 2005, 7, 893-897.
39. For a recent review on solid-phase synthesis of benzodiazepines, see: Kamal, A.; Reddy, K. L.; Devaiah, V.; Shankaraiah, N.; Reddy, D. R. Mini-Rev, Med, Chem. 2006, 6, 53-68.
40. Boojamra, C. G.; Burow, K. M,; Thompson, L. A.; Ellman, J. A. J. Org. Chem. 1997, 62, 1240-1256.
41. Web address: www.fluorous.com.