Solid-phase synthesis of natural product-like macrocycles by a sequence of Ugi-4CR and SNAr-based cycloetherification

Tetrahedron Letters

Volumn 44, Issue 30, 2003, Pages 5575-5578

  Cristau, Pierre ^a   Vors, Jean Pierre ^b   Zhu, Jieping ^a  

^a CNRS   (France)

^b BAYER AG   (Germany)

Author keywords

Biaryl ether; Macrocycle; Multicomponent reaction; SNAr cycloetherification; Solid phase synthesis; Supported isocyanide

Indexed keywords

ETHER DERIVATIVE; MACROCYCLIC COMPOUND; RESIN;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; CYCLOETHERIFICATION; DIASTEREOISOMER; DRUG SYNTHESIS; RING CLOSING METATHESIS; SUBSTITUTION REACTION; THERMODYNAMICS;

EID: 0037492348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01378-9     Document Type: Article

References (42)

1. Kase H., Kaneko M., Yamada K. J. Antibiot. 40:1987;450-454.
2. Yasuzawa T., Shirahata K., Sano H. J. Antibiot. 40:1987;455-458.
3. Sano S., Ikai K., Kuroda H., Nakamura T., Obayashi A., Ezure Y., Enomoto H. J. Antibiot. 39:1986;1674-1684.
4. Sano S., Ikai K., Katayama K., Takesako K., Nakamura T., Obayashi A., Ezure Y., Enomoto H. J. Antibiot. 39:1986;1685-1696.
5. Sano S., Ueno M., Katayama K., Nakamura T., Obayashi A. J. Antibiot. 39:1986;1697-1703.
6. For a review, see: Itokawa H., Takeya K., Hitotsuyanagi Y., Morita H. Cordell G.A. The Alkaloids. 49:1997;301-387 Academic Press, New York.
7. For reviews, see: (a) Nicolaou, K. C.; Boddy, C. N. C.; Bräse, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096-2152; (b) Williams, D; H.; Bardsley, B. Angew. Chem., Int. Ed. 1999, 38, 1172-1193; (c) Zhu, J. Exp. Opin. Ther. Pat. 1999, 9, 1005-1019.
8. For reviews, see: (a) Nicolaou, K. C.; Boddy, C. N. C.; Bräse, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096-2152; (b) Williams, D; H.; Bardsley, B. Angew. Chem., Int. Ed. 1999, 38, 1172-1193; (c) Zhu, J. Exp. Opin. Ther. Pat. 1999, 9, 1005-1019.
9. For reviews, see: (a) Nicolaou, K. C.; Boddy, C. N. C.; Bräse, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096-2152; (b) Williams, D; H.; Bardsley, B. Angew. Chem., Int. Ed. 1999, 38, 1172-1193; (c) Zhu, J. Exp. Opin. Ther. Pat. 1999, 9, 1005-1019.
10. Dinsmore C.J., Bogusky M.J., Culberson J.C., Bergman J.M., Homnick C.F., Zartman C.B., Mosser S.D., Schaber M.D., Robinson R.G., Koblan K.S., Huber H.E., Graham S.L., Hartman G.D., Huff J.R., Williams T.M. J. Am. Chem. Soc. 123:2001;2107-2108.
11. Sun X., Janvier P., Zhao G., Bienaymé H., Zhu J. Org. Lett. 3:2001;877-880.
12. Janvier P., Sun X., Bienaymé H., Zhu J. J. Am. Chem. Soc. 124:2002;2560-2567.
13. González-Zamora E., Fayol A., Bois-Choussy M., Chiaroni A., Zhu J. J. Chem. Soc., Chem. Commun. 2001;1684-1685.
14. Gámez-Montaño R., González-Zamora E., Potier P., Zhu J. Tetrahedron. 58:2002;6351-6358.
15. Janvier P., Bienaymé H., Zhu J. Angew. Chem., Int. Ed. 41:2002;4291-4294.
16. Janvier P., Bois-Choussy M., Bienaymé H., Zhu J. Angew. Chem., Int. Ed. 42:2003;811-814.
17. Dömling A., Ugi I. Angew. Chem., Int. Ed. 39:2000;3168-3210.
18. Zhu J. Synlett. 1997;133-144.
19. Cristau P., Vors J.-P., Zhu J. Org. Lett. 3:2001;4079-4082.
20. Tempest P., Ma V., Kelly M.G., Jones W., Hulme C. Tetrahedron Lett. 42:2001;4963-4968.
21. Tempest P., Pettus L., Gore V., Hulme C. Tetrahedron Lett. 44:2003;1947-1950.
22. Wang S.S. J. Am. Chem. Soc. 95:1973;1328-1333.
23. Recent examples of polymer supported UGI-4CR, see: (a) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152; (b) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (c) Szardenings, A. K.; Burkoth, T. S. Tetrahedron 1997, 53, 6573-6593; (d) Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227-7230; (e) Hulme, C.; Ma, L.; Vasant Kumar, N.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514; (f) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (g) Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 4, 1167-1170.
24. Recent examples of polymer supported UGI-4CR, see: (a) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152; (b) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (c) Szardenings, A. K.; Burkoth, T. S. Tetrahedron 1997, 53, 6573-6593; (d) Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227-7230; (e) Hulme, C.; Ma, L.; Vasant Kumar, N.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514; (f) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (g) Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 4, 1167-1170.
25. Recent examples of polymer supported UGI-4CR, see: (a) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152; (b) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (c) Szardenings, A. K.; Burkoth, T. S. Tetrahedron 1997, 53, 6573-6593; (d) Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227-7230; (e) Hulme, C.; Ma, L.; Vasant Kumar, N.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514; (f) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (g) Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 4, 1167-1170.
26. Recent examples of polymer supported UGI-4CR, see: (a) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152; (b) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (c) Szardenings, A. K.; Burkoth, T. S. Tetrahedron 1997, 53, 6573-6593; (d) Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227-7230; (e) Hulme, C.; Ma, L.; Vasant Kumar, N.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514; (f) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (g) Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 4, 1167-1170.
27. Recent examples of polymer supported UGI-4CR, see: (a) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152; (b) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (c) Szardenings, A. K.; Burkoth, T. S. Tetrahedron 1997, 53, 6573-6593; (d) Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227-7230; (e) Hulme, C.; Ma, L.; Vasant Kumar, N.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514; (f) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (g) Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 4, 1167-1170.
28. Recent examples of polymer supported UGI-4CR, see: (a) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152; (b) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (c) Szardenings, A. K.; Burkoth, T. S. Tetrahedron 1997, 53, 6573-6593; (d) Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227-7230; (e) Hulme, C.; Ma, L.; Vasant Kumar, N.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514; (f) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (g) Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 4, 1167-1170.
29. Recent examples of polymer supported UGI-4CR, see: (a) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152; (b) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (c) Szardenings, A. K.; Burkoth, T. S. Tetrahedron 1997, 53, 6573-6593; (d) Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227-7230; (e) Hulme, C.; Ma, L.; Vasant Kumar, N.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514; (f) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (g) Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 4, 1167-1170.
30. Park S.J., Keum G., Kang S.B., Koh H.Y., Kim Y. Tetrahedron Lett. 39:1998;7109-7112.
31. Burgess K., Lim D., Bois-Choussy M., Zhu J. Tetrahedron Lett. 38:1997;3345-3348.
32. Feng Y., Wang Z., Jin S., Burgess K. J. Am. Chem. Soc. 120:1998;10768-10769.
33. Kiselyov A.S., Eisenberg S., Luo Y. Tetrahedron. 54:1998;10635-19640.
34. Fotsch C., Kumaravel G., Sharma S.K., Wu A.D., Gounarides J.S., Nirmala N.R., Petter R.C. Bioorg. Med. Chem. Lett. 9:1999;2125-2130.
35. Ouyang X., Chen Z., Liu L., Dominguez C., Kiselyov A.S. Tetrahedron. 56:2000;2369-2377.
36. For recent examples, see: (a) Zhao, G.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2001, 123, 6700-6701; (b) Gámez-Montaño, R.; Zhu, J. J. Chem. Soc., Chem. Commun. 2002, 2448-2449; (c) Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047-1050.
37. For recent examples, see: (a) Zhao, G.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2001, 123, 6700-6701; (b) Gámez-Montaño, R.; Zhu, J. J. Chem. Soc., Chem. Commun. 2002, 2448-2449; (c) Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047-1050.
38. For recent examples, see: (a) Zhao, G.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2001, 123, 6700-6701; (b) Gámez-Montaño, R.; Zhu, J. J. Chem. Soc., Chem. Commun. 2002, 2448-2449; (c) Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047-1050.
39. For recent reviews, see: (a) Weber, L. Curr. Med. Chem. 2002, 9, 2085-2093; (b) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313; (c) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80; (d) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144.
40. For recent reviews, see: (a) Weber, L. Curr. Med. Chem. 2002, 9, 2085-2093; (b) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313; (c) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80; (d) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144.
41. For recent reviews, see: (a) Weber, L. Curr. Med. Chem. 2002, 9, 2085-2093; (b) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313; (c) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80; (d) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144.
42. For recent reviews, see: (a) Weber, L. Curr. Med. Chem. 2002, 9, 2085-2093; (b) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313; (c) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80; (d) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144.