Thioester-isocyanides: Versatile reagents for the synthesis of cycle–tail peptides

Chemical Communications

Volumn 48, Issue 31, 2012, Pages 3775-3777

  Rotstein, Benjamin H ^a   Winternheimer, David J ^a   Yin, Lois M ^b   Deber, Charles M ^b   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b HOSPITAL FOR SICK CHILDREN RESEARCH INSTITUTE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; MACROCYCLIC COMPOUND; PEPTIDE; THIOESTER;

ARTICLE; CYCLIZATION; SYNTHESIS;

EID: 84860192173     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc16027g     Document Type: Article

References (25)

1. Isonitrile Chemistry, ed. I. Ugi, Academic Press, New York, 1971
2. A. Dömling, I. Ugi, Angew. Chem., Int. Ed., 2000, 39, 3168
3. J. Zhu, Eur. J. Org. Chem., 2003, 1133
4. A. Dömling, Chem. Rev., 2006, 106, 17
5. R. Hili, A. K. Yudin, J. Am. Chem. Soc., 2006, 128, 14772
6. Z. He, A. K. Yudin, J. Am. Chem. Soc., 2011, 133, 13770
7. M. L. Wolfrom, J. V. Karabinos, J. Am. Chem. Soc., 1946, 68, 1455
8. T. Fukuyama, S.-C. Lin, L. Li, J. Am. Chem. Soc., 1990, 112, 7050
9. L. Benati, et al., Org. Lett., 2003, 5, 1313
10. L. Benati, et al., Synlett, 2004, 987
11. C. Savarin, J. Srogl, L. Liebeskind, Org. Lett., 2000, 2, 3229
12. H. Yang, et al., J. Am. Chem. Soc., 2007, 129, 1132
13. P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. H. Kent, Science, 1994, 266, 776
14. R. Hili, V. Rai, A. K. Yudin, J. Am. Chem. Soc., 2010, 132, 2889
15. B. H. Rotstein, V. Rai, R. Hili, A. K. Yudin, Nat. Protocols, 2010, 5, 1813
16. A. V. Gulevich, A. G. Zhdanko, R. V. A. Orru, V. G. Nenajdenko, Chem. Rev., 2010, 110, 5235
17. K. K. Kumarasamy, et al., Lancet Infect. Dis., 2010, 10, 597
18. A. X. Tran, et al., J. Biol. Chem., 2005, 280, 28186
19. N. I. Martin, et al., J. Biol. Chem., 2003, 278, 13124
20. H. M. Ellerby, D. E. Fujimura, J. Varghese, J. Med. Chem., 2008, 51, 5887
21. T. M. Hackeng, J. H. Griffin, P. E. Dawson, Proc. Natl. Acad. Sci. U. S. A., 1999, 96, 10068
22. T. Kimerlin, D. Seebach, D. Hilvert, Helv. Chim. Acta, 2002, 85, 1812
23. E. C. B. Johnson, S. B. H. Kent, J. Am. Chem. Soc., 2006, 128, 6640
24. B. H. Rotstein, R. Mourtada, S. O. Kelley, A. K. Yudin, Chem.–Eur. J., 2011, 17, 12257
25. I. Wiegland, K. Hilpert, R. E. Hancock, Nat. Protocols, 2008, 3, 163