Multiple multicomponent macrocyclizations (MiBs): A strategie development toward macrocycle diversity

Chemical Reviews

Volumn 109, Issue 2, 2009, Pages 796-814

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

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIVERSITY-ORIENTED SYNTHESIS; DRUG DEVELOPMENT; FUNCTIONAL MOTIFS; HIGH INCIDENCES; ISOCYANIDE; MACRO-CYCLIC; MACROCYCLE; MACROCYCLES; MACROCYCLIC STRUCTURES; MATERIAL SCIENCE; MULTI COMPONENTS; STRUCTURAL DIVERSITIES; SYNTHETIC METHODS;

AMINES; CYANIDES; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY;

OPTICAL DEVICES;

HETEROCYCLIC COMPOUND; MACROCYCLIC COMPOUND; PEPTOID;

CHEMICAL MODEL; CHEMISTRY; CYCLIZATION; MOLECULAR LIBRARY; REVIEW; SYNTHESIS;

CYCLIZATION; HETEROCYCLIC COMPOUNDS; MACROCYCLIC COMPOUNDS; MODELS, CHEMICAL; PEPTOIDS; SMALL MOLECULE LIBRARIES;

EID: 63849191356     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr8003407     Document Type: Review

References (112)

1. Gohlke, H.; Klebe, G. Angew. Chem., Int. Ed. 2002, 41, 2644.
2. Berg, T. Angew. Chem., Int. Ed. 2003, 42, 2462.
3. Schreiber, S. L. Science 2000, 287, 1964.
4. Boger, D. L.; Desharnais, J.; Capps, K. Angew. Chem., Int. Ed. 2003, 42, 4138.
5. Fenniri, H., Ed. Combinatorial Chemistry: A Practical Approach: Oxford University Press: New York, 2000.
6. Newman, D. J.; Cragg, G. M.; Snader, K. M. J. Nat. Prod. 2007, 70, 461.
7. Shu, Y. Z. J. Nat. Prod. 1998, 61, 1053.
8. Wessjohann, L. A.; Ruijter, E.; Rivera, D. G.; Brandt, W. Mol. Diversity 2005, 9, 171.
9. Wessjohann, L. A.; Kleber, Z.; Andrade, C.; Vercillo, O. E.; Rivera, D. G. Targets Heterocycl. Syst. 2006, 10, 24.
10. Wessjohann, L. A.; Ruijter, E. Top. Curr. Chem. 2005, 243, 137.
11. Wessjohann, L. A. Curr. Opin. Chem. Biol. 2000, 4, 303.
12. Breinbauer, R.; Vetter, I. R.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 2878.
13. Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512.
14. Driggers, E. M.; Hale, S. P.; Lee, J.; Terrett, N. K. Nat. Rev. 2008, 7, 608.
15. Rouhi, M. Chem. Eng. 2003, 81 (41), 77.
16. Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives: Wiley-VCH: Weinheim, 1995.
17. Vögtle, F. Supramolecular Chemistry: Wiley & Sons: Chichester, 1991.
18. Gutsche, C. D. In Calixarenes Revisited; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, 1998.
19. D'Souza, V. T.; Lipkowitz, K. B. Chem. Rev. 1998, 98, 1741.
20. Cram, D. J.; Cram, M. J. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, 1997.
21. Tamminen, J.; Kolehmainen, E. Molecules 2001, 6, 21.
22. Feigel, M.; Ladberg, R.; Winter, M.; Blaser, D.; Boese, R. Eur. J. Org. Chem. 2006, 371.
23. Whitmarsh, S. D.; Redmond, A. P.; Sgarlata, V.; Davis, A. P. Chem. Commun. 2008, 3669.
24. Nicolaou, K. C.; Vourloumis. D.; Winssinger, N.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 44.
25. von Nussbaum, F.; Brands, M.; Hinzen, B.; Weingand, S.; Häbich, D. Angew. Chem., Int. Ed. 2006, 45, 5072.
26. Nicolaou, K. C.; Boddy, C. N. C.; Bräse, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096.
27. Wessjohann, L. A.; Scheid, G. O. In Organic Synthesis Highlights; Schmalz. H.-G., Ed.; Wiley-VCH: Weinheim, 2000; Vol. IV. pp 251-267.
28. (a) Wessjohann, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 715.
29. (b) Wessjohann, L. Angew. Chem. 1997, 109, 739.
30. Altmann, K.-H.; Pfeiffer, B.; Arseniyadis, S.; Pratt, B. A.; Nicolaou, K. C. ChemMedChem 2007, 2, 396-423.
31. Nicolaou, K. C.; Sasmal, P. K.; Rassias, G.; Reddy, M. V.; Altmann, K.-H.; Wartmann, M.; O'Brate, A.; Giannakakou, P. Angew. Chem., Int. Ed. 2003, 42, 3515.
32. Chou, T.-C.; Dong, H.; Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Tong, W. P.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 4762.
33. de la Torre, M. C.; Sierra, M. A. Angew. Chem., Int. Ed. 2004, 43, 160.
34. Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078.
35. Burke, M. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46.
36. Takahashi, T.; Kusaka, S.; Doi. T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230.
37. Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Winssinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschangar, F.; King, N. P.; Finlay, M. R. V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2097.
38. Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716.
39. Lee, D.; Sello, J. K.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 10648.
40. Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047.
41. Sello, J. K.; Andreana, P. R.; Lee, D.; Schreiber, S. L. Org. Lett. 2003, 5, 4125.
42. Cristau, P.; Vors, J.-P.; Zhu, J. Tetrahedron Lett. 2003, 44, 5575.
43. Pirali, T.; Tron, G. C.; Zhu, J. Org. Lett. 2006, 8, 4145.
44. Cristau, P.; Vors, J.-P.; Zhu, J. QSAR Comb. Sci. 2006, 25, 519.
45. Bughin, C.; Zhao, G.; Bienavmé, H.; Zhu, J. Chem. Eur. J. 2006, 12, 1174.
46. de Greef, M.; Abeln, S.; Belkasmi, K.; Dömling, A.; Orru, R. V. A.; Wessjohann, L. A. Synthesis 2006, 3997.
47. Owens, T. D.; Araldi, G. L.; Nutt. R. F.; Semple, J. E. Tetrahedron Lett. 2001, 42, 6271.
48. Hebach, C.; Kazmaier, U. Chem. Commun. 2003, 596.
49. Dietrich, S. A.; Banfi, L.; Basso, A.; Damonte, G.; Guanti, G.; Riva, R. Org. Biomol. Chem. 2005, 3, 97.
50. Wessjohann, L. A.; Ruijter, E. Mol. Diversity 2005, 9, 159.
51. (a) Wessjohann, L. A.; Voigt, B.; Rivera, D. G. Angew. Chem., Int. Ed. 2005, 44, 4785.
52. (b) Wessjohann, L. A.; Voigt, B.; Rivera, D. G. Angew. Chem. 2005, 117, 4863.
53. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
54. Ugi, I.; Steinbrückner, C. Chem. Ber. 1961, 64, 734.
55. Dömling, A. Chem. Rev. 2006, 106, 17.
56. Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
57. Ugi, I. Pure Appl. Chem. 2001, 73, 187.
58. Banfi, L.; Riva, R. Org. React. 2005, 65, 1.
59. Weber, L. Drug Discovery Today 2002, 2, 143.
60. Bienavmé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
61. Zhu, L: Bienvamé, H. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005.
62. Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471.
63. Zhu, J. Eur. J. Org. Chem. 2003, 1133.
64. Skorna, G.; Ugi, I. Chem. Ber. 1978, 111, 3965.
65. Failli, A.; Immer, H.; Götz, M. D. Can. J. Chem. 1979, 57, 3257.
66. Vercillo, O. E.; Kleber, Z.; Andrade, C.; Wessjohann, L. A. Org. Lett. 2008, 10 (2), 205.
67. Orru, R. V. A.; de Greef, M.; Abeln, S.; Belkasmi, K.; Dömling, A.; Wessjohann, L. A. In The 12th European Symposium on Organic Chemistry (ESOC 12), 2001, 0-36, Groningen, The Netherlands.
68. Gournelis, D. C.; Laskaris, G. G.; Verpoorte, R. Nat. Prod. Rep. 1997, 14, 75.
69. Cristau, P.; Temal-Laïb, T.; Bois-Choussy, M.; Martin, M.-T.; Vors, J.-P.; Zhu, J. Chem. Eur. J. 2005, 11, 2668.
70. Temal-Laib, T.; Chastanet, J.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 583.
71. Voigt, B.; Schaks, A.; Bögel, M.; Brandt, W.; Wessjohann, L. A. In 2nd International Conference on Multi Component Reactions, Combinatorial and Related Chemistry (MCR 2003), 2003, Genova, Italy.
72. Virtanen, E.; Kolehmainen, E. Eur. J. Org. Chem. 2004, 3385.
73. Davis, A. P. Molecules 2007, 12, 2106.
74. Li, Y.; Dias, J. R. Chem. Rev. 1997, 97, 283.
75. Wallimann, P.; Marti, T.; Fürer. A.; Diederich, F. Chem. Rev. 1997, 97, 1567.
76. Davis, A. P.; Joss, J.-B. Coord. Chem. Rev. 2003, 240, 143.
77. Rivera, D. G.; Wessjohann, L. A. Molecules 2007, 12, 1890.
78. Hoye, T. R.; Moon, P. E. B. J. Am. Chem. Soc. 2000, 122, 4982.
79. Smith, A. B.. III; Kozmin. S. A.; Adams. C. M.; Pavone. D. V. J. Am. Chem. Soc. 2000, 122, 4984.
80. Rowan, S. J.; Hamilton, D. G.; Brandy, P. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1997, 119, 2578.
81. Singh, Y.; Sokolenko, N.; Kelso, M. J.; Gahan, L. R.; Abbenante, G.; Fairlie, D. P. J. Am. Chem. Soc. 2001, 123, 333.
82. Beck, B.; Picard, A.; Herdtweck, E.; Dömling. A. Org. Lett. 2004, 6, 39.
83. Wessjohann, L. A.; Rivera, D. G.; Coll, F. J. Org. Chem. 2006, 71, 7521.
84. Schreiber, S. L. Chem. Eng. News 2003, 81, 51.
85. Lehn, J.-M. In Supramolecular Science: Where It Is and Where It Is Going; Ungaro, R., Dalcanale, E., Eds.; Kluwer: Dordrecht, 1999; pp 287-304.
86. Kreye, O.; Westermann, B.; Rivera, D. G.; Johnson, D. V.; Orru, R. V. A.; Wessjohann, L. A. QSAR Comb. Sci. 2006, 25, 461.
87. Rivera, D. G.; Vercillo, O. E.; Wessjohann, L. A. Synlett 2007, 308.
88. Wessjohann, L. A.; Rivera. D. G.; León, F. Org. Lett. 2007, 9, 4733.
89. Michalik. D.; Schaks, A.; Wessjohann, L. A. Eur. J. Org. Chem. 2007, 149.
90. Westermann, B.; Michalik, D.; Schaks, A.; Kreye, O.; Wagner, C.; Merzweiler, K.; Wessjohann, L. A. Heterocycles 2007, 73, 863.
91. Janvier, P.; Bois-Choussv, M.; Bienaymé, H.; Zhu, J. Angew. Chem., Int. Ed. 2003, 42, 811.
92. (a) Ercolani, G.; Mandolini, L.; Mencarelli. P.; Roelens, S. J. Am. Chem. Soc. 1993, 115, 3901.
93. (b) Cort, A. D.; Ercolani, G.; Iamiceli, A. L.; Mandolini, L.; Mencarelli, P. J. Am. Chem. Soc. 1994, 116, 7081.
94. (c) Blankenstein, J.; Zhu, J. Eur. J. Org. Chem. 2005, 1949.
95. Rivera, D. G.; Vercillo. O. E.; Wessjohann, L. A. Org. Biomol. Chem. 2008, 1787.
96. Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898.
97. Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J.-L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, 3652.
98. León, R: Rivera, D. G.; Wessjohann, L. A. J. Org. Chem. 2008, 73, 1762.
99. Sierra, M. A.; Pellico, D.; Gómez-Gallego, M.; Manchego, M. J.; Torres, R. J. Org. Chem. 2006, 71, 8787.
100. Arumugan, N.; Raghunathan, R. Tetrahedron Lett. 2006, 47, 8855.
101. Zhao, G.; Sun, X.; Bienaymé, H.; Zhu, J. Am. Chem. Soc. 2001, 123, 6700.
102. Jin, Z. Nat. Prod. Rep. 2003, 20, 584.
103. Petasis, N. A. In Multicomponent Reactions; Zhu, J., Bienyamé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005; pp 119-123.
104. Alfonso, I.; Boite, M.; Bru, M.; Burguete, M. I.; Luis, S. V.; Rubio, J. J. Am. Chem. Soc. 2008, 130, 6137-6144.
105. Christinat, N.; Scopellit, R.; Severin, K. J. Org. Chem. 2007, 72, 2192.
106. Lin, J.-B.; Xu, X.-N.; Jiang, X.-K.; Li. Z.-T. J. Org. Chem. 2008, 73, 9403.
107. Rivera, D. G.; Wessjohann, L. A. J. Am. Chem. Soc. 2006, 128, 7122.
108. Llinares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57.
109. Bowman-James, K. Acc. Chem. Res. 2005, 38, 671.
110. Rivera, D. G.; Wessjohann, L. A. J. Am. Chem. Soc. 2009, submitted for publication.
111. Akritopoulus-Zanze, I.; Djuric, S. W. Heterocycles 2007, 73, 125.
112. Eckert, H. Heterocycles 2007, 73, 149.