Synthesis of backbone modified cyclic peptides bearing dipicolylamino sidearms

Tetrahedron

Volumn 67, Issue 5, 2011, Pages 1019-1029

  Butler, Stephen J ^a   Jolliffe, Katrina A ^a   Lee, Wee Yu Gladys ^a   McDonough, Matthew J ^a   Reynolds, Aaron J ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Cyclic peptide; Macrocycle; Oxazole

Indexed keywords

AMINE; CYCLOPEPTIDE; DIPICOLINIC ACID; MACROCYCLIC COMPOUND; ORNITHINE; OXAZOLE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; EPIMERIZATION; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

LISSOCLINUM;

EID: 78651355104     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.100     Document Type: Article

References (31)

1. J.W. Steed, and J.L. Atwood Supramolecular Chemistry 2000 John Wiley, Ltd Chichester, UK
2. K. Gloe, Macrocyclic Chemistry: Current Trends and Future Perspectives 2005 Springer Dordrecht
3. P. Wipf S.W. Pelletier, Alkaloids: Chemical and Biological Perspectives 1998 Elsevier Amsterdam 187 228
4. D. Mink, S. Mecozzi, and J. Rebek Jr. Tetrahedron 39 1998 5709
5. K.A. Jolliffe Supramol. Chem. 17 2005 81
6. A. Pintér, and G. Haberhauer Eur. J. Org. Chem. 2008 2375
7. A. Pintér, G. Haberhauer, I. Hyla-Kryspin, and S. Grimme Chem. Commun. 2007 3711
8. G. Haberhauer, T. Oeser, and F. Romiger Chem. Commun. 2005 2799
9. G. Haberhauer, T. Oeser, and F. Romiger Chem. - Eur. J. 11 2005 6718
10. E. Ziegler, and G. Haberhauer Eur. J. Org. Chem. 2009 3432
11. Y. Singh, M.J. Stoermer, A.J. Lucke, M.P. Glenn, and D.P. Fairlie Org. Lett. 4 2002 3367
12. Y. Singh, M.J. Stoermer, A.J. Lucke, T. Guthrie, and D.P. Fairlie J. Am. Chem. Soc. 127 2005 6563
13. S.C. Ceide, L. Trembleau, G. Haberhauer, L. Somogyi, X. Lu, T. Bartfai, and J. Rebek Jr. Proc. Natl. Acad. Sci. U.S.A. 101 2004 16727
14. Á Pintér, and G. Haberhauer Synlett 2009 3082
15. M.J. McDonough, A.J. Reynolds, W.Y.G. Lee, and K.A. Jolliffe Chem. Commun. 2006 2971
16. A.J. Lucke, J.D.A. Tyndall, Y. Singh, and D.P. Fairlie J. Mol. Graph. Model. 21 2003 341
17. G. Haberhauer, A. Pinter, T. Oeser, and F. Rominger Eur. J. Org. Chem. 2007 1779
18. G. Haberhauer, and F. Rominger Eur. J. Org. Chem. 2003 3209
19. A.I. Meyers, and F.X. Tavares J. Org. Chem. 61 1996 8207
20. D.J. Freeman, and G. Pattenden Tetrahedron Lett. 39 1998 3251
21. K.M. DiVittorio, J.R. Johnson, E. Johansson, A.J. Reynolds, K.A. Jolliffe, and B.D. Smith Org. Biomol. Chem. 4 2006 1966
22. A.J. Phillips, Y. Uto, P. Wipf, M.J. Reno, and D.R. Williams Org. Lett. 2 2000 1165
23. A. Bertram, A.J. Blake, F. Gonzaléz-López de Turiso, J.S. Hannam, K.A. Jolliffe, G. Pattenden, and M. Skae Tetrahedron 59 2003 6979
24. G.R. Sullivan, J.A. Dale, and H.S. Mosher J. Org. Chem. 38 1973 2143
25. K. Yonetani, Y. Hirotsu, and T. Shiba Bull. Chem. Soc. Jpn. 48 1975 3302
26. A.B. Smith III, G.K. Friestad, J. Barbosa, E. Bertounesque, J.J.-W. Duan, K.G. Hull, M. Iwashima, Y. Qiu, P.G. Spoors, and B.A. Salvatore J. Am. Chem. Soc. 121 1999 10478
27. J.A. Bull, E.P. Balskus, R.A.J. Horan, M. Langner, and S.V. Ley Angew. Chem., Int. Ed. 45 2006 6714
28. The analogous threonine derived oxazole has been reported previously and no detectable epimerisation was reported. See: R.J. Black, V.J. Dungan, R.Y.T. Li, P.Y. Young, and K.A. Jolliffe Synlett 2010 551
29. Use of our standard conditions (4 M HCl/dioxane) resulted in partial Cbz deprotection.
30. L.X. Wang, M. Tang, T. Suzuki, K. Kitajima, Y. Inoue, S. Inoue, J.Q. Fan, and Y.C. Lee J. Am. Chem. Soc. 119 1997 11137
31. P.M.T. Ferreira, H.L.S. Maia, L.S. Monterio, and J. Sacramento J. Chem. Soc., Perkin Trans. 1 1999 3697