Efficient construction of the carbon skeleton of the novel polyoxazole-based cyclopeptide IB-01211 via a biomimetic macrocyclisation

Synlett

Volumn , Issue 4, 2010, Pages 555-558

  Chattopadhyay, Shital K ^a   Singha, Sovan K ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

Biomimetic; Heterocycles; Macrocyclisation; Oxazoles; Peptides

Indexed keywords

CARBON; CYCLOPEPTIDE; IB 01211; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PROCESS DEVELOPMENT; STRUCTURE ANALYSIS;

EID: 77955383480     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219180     Document Type: Article

References (33)

1. For reviews see: (a) Pattenden, G. J. Heterocycl. Chem. 1992, 29, 607.
2. (b) Faulkner, D. J. Nat. Prod. Rep. 2002, 29, 1; and earlier reports in the series.
3. (c) Yeh, V. S. C. Tetrahedron 2004, 60, 11995.
4. (d) Bertram, A.; Pattenden, G. Nat. Prod. Rep. 2007, 24, 18.
5. (e) Hughes, R. A.; Moody, C. J. Angew. Chem. Int. Ed. 2007, 46, 2.
6. For some examples, see: (a) Gonzalez, M. A.; Pattenden, G. Angew. Chem. Int. Ed. 2003, 42, 1255.
7. (b) Krebs, O.; Taylor, R. J. K. Org. Lett. 2005, 7, 1063.
8. (c) Bagley, M. C.; Chapaneri, K.; Dale, J. W.; Xiong, X.; Bower, J. J. Org. Chem. 2005, 70, 1389.
9. (d) Bagley, M. C.; Bashford, K. E.; Hesketh, C. L.; Moody, C. J. J. Am. Chem. Soc. 2000, 122, 3301.
10. (e) Mann, E.; Kessler, H. Org. Lett. 2003, 5, 4567.
11. (f) Burgett, A. W. G.; Li, Q.; Wei, Q.; Harran, P. G. Angew. Chem. Int. Ed. 2003, 42, 4961.
12. (g) Liu, P.; Panek, J. S. J. Am. Chem. Soc. 2000, 122, 1235.
13. Deeley, J.; Pattenden, G. Chem. Commun. 2005, 797.
14. Kanoh, K.; Matsuo, Y.; Adachi, K.; Imagawa, H.; Nishizawa, M.; Shizuri, Y. J. Antibiot. 2005, 58, 289.
15. Shin-Ya, K.; Weirzba, K.; Matsuo, K.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. J. J. Am. Chem. Soc. 2001, 123, 1262.
16. Wipf, P. Chem. Rev. 1995, 95, 2115.
17. Chattopadhyay, S. K.; Pattenden, G. Synlett 1997, 1342.
18. (a) Pattenden, G.; Ashweek, N. J.; Baker-Glenn, C. A. G.; Walker, G. M.; Yee, J. G. K. Angew. Chem. Int. Ed. 2007, 46, 4359.
19. (b) Pattenden, G.; Ashweek, N. J.; Baker-Glenn, C. A. G.; Kempson, J.; Walker, G. M.; Yee, J. G. K. Org. Biol. Chem. 2008, 6, 1478.
20. (a) For related contemporaneous studies, see: Doi, T.; Yoshida, M.; Shin-Ya, K.; Takahasi, T. Org. Lett. 2006, 8, 4165.
21. (b) Deeley, J.; Bertram, A.; Pattenden, G. Org. Biol. Chem. 2008, 6, 1994.
22. (c) Marson, M. C.; Saadi, M. Org. Biol. Chem. 2006, 4, 3892.
23. Chattopadhyay, S. K.; Biswas, S. Tetrahedron Lett. 2006, 47, 7897.
24. Romero, F.; Malet, L.; Canedo, L. M.; Cuevas, C.; Reyes, J. WO 2005/000880 A2, 2005.
25. (a) Hernández, D.; Vilar, G.; Riego, E.; Cañedo, L. M.; Cuevas, C.; Albericio, F.; Álvarez, M. Org. Lett. 2007, 9, 809.
26. (b) Hernández, D.; Riego, E.; Francesch, A.; Cuevas, C.; Albericio, F.; Álvarez, M. Tetrahedron 2007, 63, 9862.
27. (c) Hernández, D.; Riego, E.; Albericio, F.; Álvarez, M. Eur. J. Org. Chem. 2008, 3389.
28. Chattopadhyay, S. K.; Biswas, S.; Ghosh, S. K. Synthesis 2008, 7897.
29. Chattopadhyay, S. K.; Biswas, S.; Pal, B. K. Synthesis 2006, 1289.
30. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604.
31. 9Si: 973.3681; found: 973.3682
32. (a) Chattopadhyay, S. K.; Kempson, J.; McNeil, A.; Pattenden, G.; Reader, M.; Rippon, D. E.; Waite, D. J. Chem. Soc., Perkin Trans. 1 2000, 2415.
33. (b) Endo, N.; Tsuboi, K.; Kim, R.; Yonezawa, Y.; Shin, C. Heterocycles 2003, 60, 1567.