One-step synthesis of natural product-inspired biaryl ether-cyclopeptoid macrocycles by double ugi multiple-component reactions of bifunctional building blocks

European Journal of Organic Chemistry

Volumn , Issue 1, 2007, Pages 149-157

  Michalik, Dirk ^a,b   Schaks, Angela ^a   Wessjohann, Ludger A ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Biaryl ether; Cyclopeptide; Macrocyclization; Multiple component reaction; Peptoid; Ugi reaction

Indexed keywords

EID: 33846073927     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600354     Document Type: Article

References (36)

1. a) U. Nubbemeyer, Top. Curr. Chem. 2001, 216, 125-196;
2. b) Y. Z. Shu, J. Nat. Prod. 1998, 61, 1053-1071;
3. c) D. J. Newman, G. M. Cragg, K. M. Snader, Nat. Prod Rep. 2000, 17, 215-234.
4. Recent reviews: a) J. Blankenstein, J. Zhu, Eur. J. Org. Chem. 2005, 1949-1964;
5. b) L. A. Wessjohann, E. Ruijter, Top. Curr. Chem. 2005, 243, 137-184 (Ed.: J. H. Mulzer), Springer, Heidelberg 2005, 137-184;
6. c) L. A. Wessjohann, E. Ruijter, D. Garcia-Rivera, W. Brandt, Mol. Diversity 2005, 9, 171-186;
7. d) L. A. Wessjohann, E. Ruijter, Mol. Diversity 2005, 9, 159-169;
8. e) R. Breinbauer, I. R. Vetter, H. Waldmann, Angew. Chem. 2002, 114, 3002-3015;
9. Angew. Chem. Int. Ed. 2002, 41, 2878-2890;
10. f) K. S. Yeung, I. Paterson, Angew. Chem. 2002, 114, 4826-4847;
11. Angew. Chem. Int. Ed. 2002, 41, 4632-4653;
12. g) J. Nielsen, Curr. Opin. Chem. Biol. 2002, 6, 297-305;
13. h) L. A. Wessjohann, Curr. Opin. Chem. Biol. 2000, 4, 303-309;
14. i) P. Wipf, Chem. Rev. 1995, 95, 2115-2134;
15. j) M. A. Koch, H. Waldmann, Drug Disc. Today 2005, 10, 471-482.
16. Selected references: a) Z. J. Gartner, B. N. Tse, R. Grubina, J. B. Doyon, T. M. Snyder, D. R. Liu, Science 2004, 305, 1601-1605;
17. b) W. J. N. O'David, H. Meester, H. E. Bieraugel, H. E. Schoemaker, H. Hiemstra, J. H. van Maarseveen, Angew. Chem. 2003, 115, 4509-4511;
18. Angew. Chem. Int. Ed. 2003, 42, 4373-4375;
19. c) B. Beck, G. Larbig, B. Mejat, M. Magnin-Lachaux, A. Picard, E. Herdtweck, A. Dömling, Org. Lett. 2003, 5, 1047-1050;
20. d) P. Cristau, J.-P. Vors, J. Zhu, Org. Lett. 2001, 3, 4079-4082;
21. e) U. Schmidt, J. Langner, J. Pept. Res. 1997, 49, 67-73;
22. f) A. Ehrlich, H.-U. Heyne, R. Winter, M. Beyermann, H. Haber, L. A. Carpino, M. Bienert, J. Org. Chem. 1996, 61, 8831-8838.
23. M. C. F. Monnee, A. J. Brouwer, L. M. Verbeek, A. M. A. van Wageningen, R. M. J. Liskamp, Bioorg. Med. Chem. Lett. 2001, 11, 1521-1525.
24. M. Perez-Gonzalez, R. F. W. Jackson, Chem. Commun. 2000, 2423-2424.
25. a) A. Bigot, M. Bois-Choussy, J. Zhu, Tetrahedron Lett. 2000, 41, 4573-4577;
26. b) J. W. Janetka, D. H. Rich, J. Am. Chem. Soc. 1997, 119, 6488-6495.
27. a) D. Ranganathan, V. Haridas, K. P. Madhusudanan, R. Roy, R. Nagaraj, G. B. John, J. Am. Chem. Soc. 1997, 119, 11578-11584;
28. b) P. Janvier, M. Bois-Choussy, H. Bienaymé, J. Zhu, Angew. Chem. 2003, 115, 835-838;
29. Angew. Chem. Int. Ed. 2003, 42, 811-814.
30. I. Ugi, U. Fetzer, U. Eholzer, H. Knupfer, K. Offermann, Angew. Chem. 1965, 77, 492-504;
31. Angew. Chem. Int. Ed. Engl. 1965, 4, 472-484.
32. Patent, Dow Chem. Co.; US 1900442; 1930.
33. J. C. Lagarias, R. A. Houghten, H. Rapoport, J. Am. Chem. Soc. 1978, 100, 8202-8209.
34. L. A. Wessjohann, B. Voigt, D. Garcia-Rivera, Angew. Chem. 2005, 117, 4863-4868;
35. Angew. Chem. Int. Ed. 2005, 44, 4785-4790.
36. L. A. Wessjohann, D. G. Rivera, F. Coll, J. Org. Chem. 2006, 71, 7521-7526.