Architectural chemistry: Synthesis of topologically diverse macromulticycles by sequential multiple multicomponent macrocyclizations

Journal of the American Chemical Society

Volumn 131, Issue 10, 2009, Pages 3721-3732

  Rivera, Daniel G ^a,b   Wessjohann, Ludger A ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b UNIVERSITY OF HAVANA   (Cuba)

Author keywords

[No Author keywords available]

Indexed keywords

ADVANCED PROTOCOLS; BIFUNCTIONAL; BUILDING BLOCKES; CRYPTANDS; MACRO-CYCLIZATION; MULTICOMPONENTS; NONSYMMETRIC; ONE POT; REACTION SEQUENCES; SEQUENTIAL APPROACH; TERTIARY AMIDES; TETHER CHAIN;

AMIDES;

FUNCTIONAL GROUPS;

AMIDE; CARBROMAL; CRYPTAND; DIAMINE; MACROCYCLIC COMPOUND; PEPTOID; STEROID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; COVALENT BOND; CYCLIZATION; DEPROTECTION REACTION; MOLECULAR RECOGNITION; ONE POT SYNTHESIS; PURIFICATION; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; CHEMISTRY;

CYCLIZATION; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE;

EID: 70249101396     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809005k     Document Type: Article

References (72)

1. (a) Schneider. H.-J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; Wiley: Chichester, 2000.
2. (b) Cram, D. J.; Cram, M. J. Container Molecules and Their Guests; The Royal Society of Chemistry: Cambridge, 1994.
3. (c) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; Wiley-VCH: Weinheim, 1995.
4. (d) Vögtle, F. Supramolecular Chemistry: An Introduction; Wiley & Sons: New York, 1993.
5. (a) Felder, T. Schalley, C.A. Artificial Rotary Motors Based on Rotaxanes. In Highlights in Bioorganic Chemistry; Wennemers, H., Schmuck, C., Eds.; Wiley-VCH: Weinheim, 2004; p 256.
6. (b) Balsani, V.; Venturi, N.; Credi, A. Molecular devices and machines: A journey into the nanoworld; Wiley-VCH: Weinheim, 2003.
7. For reviews on templated and nontemplated macrocyclization strategies, see:(a) Zhang, W.; Moore, J. S. Angew. Chem., Int. Ed. 2006, 45, 4416-4439.
8. (b) Laughrey, Z. R.; Gibb, B. C. Top. Curr. Chem. 2005, 249, 67-125.
9. (c) Arico, F.; Badjic, J. D.; Cantrill, S. J.; Flood, A. H.; Leung, K. C.-R; Liu, Y.; Stoddart, J. F. Top. Curr. Chem. 2005. 249, 203-269.
10. (d) Dietrich-Buchecker, C:; Colasson, B. X.; Sauvage. J.-P. Top. Curr. Chem. 2005, 249, 261-283.
11. (e) Wessjohann. L. A.; Ruijter, E. Top. Curr. Chem. 2005, 243, 137-184.
12. (f) Schalley, C. A.; Wielandt, T.; Bruggemann. J.; Vögtle, F. Top. Curr. Chem. 2004, 248, 141-200.
13. (g) Vilar, R. Angew. Chem., Int. Ed. 2003, 42, 1460-1477.
14. (h) Rowan. S. J.; Cantrill, S. J.; Cousin. G. R. L.; Sanders. J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898-952.
15. (i) Gerbeleu, N. V.; Arion, V. B.; Burgess, J. Template Synthesis of Macrocyclic Compounds; Wiley-VCH: Weinheim, 1999.
16. (j) Seel, C; Vogtle, F. Angew. Chem., Int. Ed. 1992, 31, 528-549.
17. (a) Rivera, D. G.; Vercillo, O. E.; Wessjohann, L. A. Org. Biomol. Chem. 2008, 6, 1787-1795.
18. (b) León, F.; Rivera, D. G.; Wessjohann, L. A. J. Org. Chem. 2008, 73, 1762-1767.
19. (c) Michalik, D.; Schaks. A.; Wessjohann, L. A. Eur. J. Org. Chem. 2007. 14. 9-157.
20. (d) Wessjohann, L. A.; Rivera, D. G.; Coll, F. J. Org. Chem. 2006, 71, 7521-7526.
21. (e) Wessjohann, L. A.; Voigt, B.; Rivera, D. G. Angew. Chem., Int. Ed. 2005, 44, 4785-1790.
22. (f) Wessjohann, L. A.; Ruijter, E. Mol. Diversity 2005, 9, 159-169.
23. (g) Wessjohann, L. A.: Rivera, D. G.; Vercillo, E. O. Chem. Rev. 2009, 109, 796-814.
24. (a) Rivera, D. G.; Wessjohann. L. A. J. Am. Chem. Soc. 2006. 128, 7122-7123.
25. (b) Rivera, D. G.; Vercillo. O. E.; Wessjohann, L. A. Synlett 2007, 308, 312.
26. (c) Wessjohann, L. A.; Rivera, D. G.; Leon, F. Org. Lett. 2007, 9, 4733-4736.
27. For reviews on cryptand chemistry, see ref 1 and: (a) Amendola, V.; Bonizzoni. M.; Esteban-Gómez, D.; Fabbrizzi, L.; Licchelli, M.; Sancenón, F.; Taglietti, A. Coord. Chem. Rev. 2006, 250, 1451-1470.
28. (b) Bowman-James, K. Acc. Chem. Res. 2005. 38, 671-678.
29. (c) McKee, V.; Nelson, J.; Town, R. M. Chem. Soc. Rev. 2003, 32, 309-325.
30. (d) Amendola. V.; Fabbrizzi, L.; Mangano. C.; Pallavacini, P.; Poggi, A.: Taglietti, A. Coord. Chem. Rev. 2001, 219-221, 821-837.
31. (e) Llinares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57-75.
32. (f) Lehn, J.-M. Pure Appl. Chem. 1980, 52, 2442-2459.
33. (g) Lehn, J.-M. Pure Appl. Chem. 1978, 52, 871-892.
34. (a) Koshabek, R.; Gleiter. R.; Rominger, F. Eur. J. Inorg. Chem. 2006, 60, 9-620.
35. (b) Rev. D.; Bharadwaj, P. K. Eur. J. Inorg. Chem. 2006, 177, 1-1776.
36. (c) Huang, F.; Slebodnick, C.; Switeck. K. A.; Gibson, H. W. Chem. Commun. 2006, 1929, 1931.
37. (d) Mukhopadhyay, P.: Sarkar, B.; Bharadwaj, P. K.; Nättinen, K.: Rissanen, K. Inorg. Chem. 2003, 42, 4955-4960.
38. (e) Sarkar, B.; Mukhopadhyay, P.; Bharadwaj, P. K. Coord. Chem. Rev. 2003, 236, 1-13.
39. (f) Plenio, H.; El-Desoky, H.; Heinze, J. Chem. Ber, 1993, 126, 2403-2408.
40. For selected examples of cryptands being really nonsymmetric, see: (a) Tönsoff, C.; Merz, K.; Bucher. G. Org. Biomol. Chem. 2005, 3, 303-308.
41. (b) Esteban, D.; Bañobre, D.; de Bias, A.; Rodríguez-Bias, T.; Bastida, R.; Macías, A.; Rodríguez, A.; Fenton, D. E.; Adams, H.; Mahía, J. Eur. J. Inorg. Chem. 2000, 144, 5-1456.
42. (e) Kranemann, C; Eilbracht, P. Eur. J. Org. Chem. 2000, 236, 7-2377.
43. Richman. E. J.; Atkins, T. J. J.Am. Chem. Soc. 1974, 96, 2268-2270.
44. (a) Dömling, A. Chem. Rev. 2006, 106, 17-89.
45. (b) Multicomponent Reactions; Zhu, J., Brenyamé, H., Eds.; Wiley-VCH: Weinheim, 2005.
46. (c) Dömling, A.; Ugi. I.Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
47. For reviews on amide-based receptors, see: (a) Gibson, S. E.; Lecci. C. Angew. Chem., Int. Ed. 2006, 45, 1364-1377.
48. (b) Kang, S. O.; Hossain, M. A.; Bowman-James, K. Coord. Chem. Rev. 2006, 250, 3038-3052.
49. (c) Davis, A. P.;James, T. D. Carbohydrate receptors. In Functional Synthetic Receptors; Schrader, T., Hamilton, A. D., Eds.; Wiley-VCH: Weinheim, 2005; pp 45-109.
50. (d) Bondy, C. R.; Loeb, S. J. Coord. Chem. Rev. 2003, 240, 77-99.
51. (e) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40. 486-516.
52. Nakanishi, K.; Berova, N.; Woody, R. W. Circular Dichroism; Wiley- VCH: Weinheim, 1994.
53. For reviews on the use of steroids in molecular recognition, see: (a) Davis, A. P. Molecules 2007,12, 2106-2122.
54. (b) Davis, A. P. Coord. Chem. Rev. 2006, 250, 2939-2951.
55. (c) Virtanen. E.; Kolehmainen. E. Eur. J. Org. Chem. 2004, 338, 5-3399.
56. (d) Davis, A. P.; Joss, J.-B. Coord. Chem. Rev. 2003, 240, 143-156.
57. (e) Tamminen. J.; Kolehmarnen, E. Molecules 2001, 6, 21-46.
58. (f) Wallimann, P.; Marti, T.; Fürer, A.; Drederich, F. Chem. Rev. 1997, 97. 1567-1608.
59. For selected reports on cholane-based macrocycles, see refs 4, 5, and: (a) Whitmarsh, S. D.; Redmond. A. P.; Sgarlata, V.; Davis, A. P. Chem. Commun. 2008, 366, 9-3671.
60. (b) Feigel, M.: Ladberg, R.: Engels, S.; Herbst-Irmer, R.; Fröhlich, R. Angew. Chem., Int. Ed. 2006, 45, 5698-5702.
61. (c) Fergel, M.; Ladberg, R.; Winter, M.; Bläser, D.; Boese, R. Eur. J. Org. Chem. 2006, 371-377.
62. (d) Srsson. A. L.; Clare. J. P.; Davis, A. P. Chem. Commun. 2005, 5263, 5265.
63. (e) Babu, P.; Maitra, U. Proc. Indian Acad. Sci. (Chem. Sci.) 2003, 115, 607-612.
64. (f) Virtanen. E.; Koivukorpi, J.; Tamminen. J.; Mänttäti, P.; Kolehmainen. E. J. Organomet. Chem. 2003, 668, 43-50.
65. (g) Dias, J. R.; Pascal, R. A.; Morrill. J.; Holder. A. J.; Gao, H.; Barnes, C. J. Am. Chem. Soc. 2002, 124, 4647-4652.
66. (h) Albert, D.; Feigel, M.; Benet-Buchholz, J.; Boese, R. Angew. Chem., Int. Ed. 1998, 37, 2727-2729.
67. Barry, J. F.; Davis, A. P.; Pérez-Payán, M. N. Tetrahedron Lett. 1999, 40, 2849-2852.
68. (a) Klein. E.; Ferrand, Y.: Auty. E. K.; Davis, A. P. Chem. Commun. 2007, 2390, 2392.
69. (b) Ferrand, Y.; Cramp. M. P.; Davis, A. P. Science 2007, 318, 619-622.
70. For a preliminary account on parts of the tetramacrocyclic work, see ref 5a.
71. Doggers, E. M.; Hale, S. P.; Lee, J.; Terrett, N. K. Nat. Rev. 2008, 7, 608-624.
72. Batta, A. K.; Aggarwal, S. K.; Salen, G.; Shefer, S. J.LipidRes. 1991, 32, 977-983.