Combinatorial synthesis of macrocycles by multiple multicomponent macrocyclization including bifunctional building blocks (MiB)

Synlett

Volumn , Issue 2, 2007, Pages 308-312

  Rivera, Daniel G ^a   Vercillo, Otilie E ^a   Wessjohann, Ludger A ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

Combinatorial synthesis; Cryptands; Macrocycles; Multicomponent reactions; Ugi reaction

Indexed keywords

MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; CYCLIZATION; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33847080442     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-968006     Document Type: Article

References (34)

1. (a) Gibson, S. E.; Lecci, C. Angew. Chem. Int. Ed. 2006, 45, 1364.
2. (b) Wessjohann, L. A.; Ruijter, E.; Rivera, D. G.; Brandt, W. Mol. Diversity 2005, 9, 171.
3. (c) Arico, S.; Chang, T.; Cantrill, S. J.; Khan, S. I.; Stoddart, J. F. Chem. Eur. J. 2005, 11, 4655.
4. (d) Schalley, C. A.; Wielandt, T.; Bruggeman, J.; Vögtle, F. Top. Curr. Chem. 2004, 248, 141.
5. (e) Newman, D. J.; Cragg, G. M.; Snader, K. M. Nat. Prod. Rep. 2000, 17, 215.
6. (a) Wessjohann, L. A.; Ruijter, E. Top. Curr. Chem. 2005, 243, 137.
7. (b) Blankenstein, J.; Zhu, J. Eur. J. Org. Chem. 2005, 1949.
8. (c) Nicolaou, K. C. J. Org. Chem. 2005, 70, 7007.
9. (d) Schalley, C. A.; Reckien, W.; Baytekin, B.; Vögtle, F. Chem. Eur. J. 2004, 10, 4777.
10. (e) Lambert, J. N.; Mitchell, J. P.; Roberts, K. D. J. Chem. Soc., Perkin Trans. 1 2001, 471.
11. (f) de Greef, M.; Abeln, S.; Belkasmi, K.; Dömling, A.; Orru, R. V. A.; Wessjohann, L. A. Synthesis 2006, 3977.
12. (a) Boger, D. L.; Desharnais, J.; Capps, K. Angew. Chem. Int. Ed. 2003, 42, 4138.
13. (b) Combinatorial Chemistry: A Practical Approach; Fenniri, H., Ed.; Oxford University Press: New York, 2000.
14. (a) Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J.-L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, 3652.
15. (b) Rowan, S. J.; Cantrill, S. J.; Cousin, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem. Int. Ed. 2002, 41, 898.
16. (a) Rivera, D. G.; Wessjohann, L. A. J. Am. Chem. Soc. 2006, 128, 7122.
17. (b) Wessjohann, L. A.; Voigt, F.; Rivera, D. G. Angew. Chem. Int. Ed 2005, 44, 4785.
18. (c) Wessjohann, L. A.; Ruijter, E. Mol. Diversity 2005, 9, 159.
19. (d) Wessjohann, L. A.; Rivera, D. G.; Coll, F. J. Org. Chem. 2006, 71, 7521.
20. (e) Michalik, D.; Schaks, A.; Wessjohann, L. A. Eur. J. Org. Chem. 2007, 149.
21. (a) Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047.
22. (b) Sello, J. K.; Andreana, P. R.; Lee, D.; Schreiber, S. L. Org. Lett. 2003, 5, 4125.
23. (c) Cristau, P.; Vors, J.-P.; Zhu, J. Tetrahedron Lett. 2003, 44, 5575.
24. (d) Owens, T. D.; Araldi, G. L.; Nutt, R. F.; Semple, J. E. Tetrahedron Lett. 2001, 42, 6271.
25. (e) Zhao, G.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2001, 123, 6700.
26. (a) Dömling, A. Chem. Rev. 2006, 106, 17.
27. (b) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
28. Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512.
29. Brahmachary, E.; Ling, F. H.; Svec, F.; Fréchet, J. M. J. J. Comb. Chem. 2003, 5, 441; and references therein.
30. (a) Bowman-James, K. Acc. Chem. Res. 2005, 38, 671.
31. (b) Llinares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57.
32. (c) Amendola, V.; Fabbrizzi, L.; Mangano, C.; Pallavacini, P.; Poggi, A.; Taglietti, A. Coord. Chem. Rev. 2001, 219-221, 821.
33. (d) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; Wiley-VCH: Weinheim, 1995.
34. (e) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823.