A de novo approach to the synthesis of glycosylated methymycin analogues with structural and stereochemical diversity

Organic Letters

Volumn 12, Issue 22, 2010, Pages 5150-5153

  Borisova, Svetlana A ^b   Guppi, Sanjeeva R ^a   Kim, Hak Joong ^b   Wu, Bulan ^a   Penn, John H ^a   Liu, Hung Wen ^b   O'Doherty, George A ^c  

^a WEST VIRGINIA UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^c NORTHEASTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; MACROLIDE; METHYMYCIN; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; GLYCOSYLATION; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; GLYCOSYLATION; MACROLIDES; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM; STREPTOMYCES;

EID: 78449303571     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102144g     Document Type: Article

References (46)

1. Rawlings, B. J. Nat. Prod. Rep. 2001, 18, 190-227
2. Rawlings, B. J. Nat. Prod. Rep. 2001, 18, 231-281
3. Staunton, J.; Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380-416
4. Walsh, C. Antibiotics: Actions, Origins, Resistance; ASM Press: Washington, D.C., 2003.
5. Weissman, K. J. Philos. Trans. R. Soc. London, Ser. A 2004, 362, 2671-2690
6. Donin, M. N.; Pagano, J.; Dutcher, J. D.; McKee, C. M. Antibiot. Annu. 1953-1954, 1, 179-185
7. Djerassi, C.; Zderic, J. A. J. Am. Chem. Soc. 1956, 78, 6390-6395
8. Xue, Y.; Zhao, L.; Liu, H.-w.; Sherman, D. H. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12111-12116
9. Weymouth-Wilson, A. C. Nat. Prod. Rep. 1997, 14, 99-110
10. Thorson, J. S.; Hosted, J.; Jiang, J.; Biggins, J. B.; Ahlert, J. Curr. Org. Chem. 2001, 5, 139-167
11. Kren, V.; Martinkova, L. Curr. Med. Chem. 2001, 8, 1303-1328
12. He, X. M.; Liu, H.-w. Annu. Rev. Biochem. 2002, 71, 701-754
13. Thibodeaux, C. J.; Melancon, C. E., III; Liu, H.-w. Nature 2007, 446, 1008-1016
14. Thibodeaux, C. J.; Melancon, C. E., III; Liu, H.-w. Angew. Chem., Int. Ed. 2008, 47, 9814-9859
15. Borisova, S. A.; Zhao, L.; Sherman, D. H.; Liu, H.-w. Org. Lett. 1999, 1, 133-136
16. Velvadapu, V.; Andrade, R. B. Carbohydr. Res. 2008, 343, 145-150
17. Packard, G. K.; Scott, D.; Rychnovsky, S. D. Org. Lett. 2001, 3, 3393-3396
18. Mendez, C.; Salas, J. A. Trends Biotechnol. 2001, 19, 449-456
19. Griffith, B. R.; Langenhan, J. M.; Thorson, J. S. Curr. Opin. Biotechnol. 2005, 16, 622-630
20. Melançon, C. E.; Thibodeaux, C.; Liu, H.-w. ACS Chem. Biol. 2006, 1, 499-504
21. Mendez, C.; Luzhetskyy, A.; Bechthold, A.; Salas, J. A. Curr. Top. Med. Chem. 2008, 8, 710-724
22. Williams, G. J.; Gantt, R. W.; Thorson, J. S. Curr. Opin. Chem. Biol. 2008, 12, 556-564
23. Babu, R. S.; O'Doherty, G. A. J. Am. Chem. Soc. 2003, 125, 12406-12407
24. Comely, A. C.; Eelkema, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 8714-8715
25. Kim, H.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 1336-1337
26. Babu, R. S.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2004, 126, 3428-3429
27. Harris, J. M.; Keranen, M. D.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2982-2983
28. Harris, J. M.; Keranen, M. D.; Nguyen, H.; Young, V. G.; O'Doherty, G. A. Carbohydr. Res. 2000, 328, 17-36 For its use in oligosaccharide synthesis, see: Guo, H.; O'Doherty, G. A. Angew. Chem., Int. Ed. 2007, 46, 5206-5208
29. Zhou, M.; O'Doherty, G. A. Org. Lett. 2008, 10, 2283-2286
30. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522
31. Li, M.; Scott, J. G.; O'Doherty, G. A. Tetrahedron Lett. 2004, 45, 1005-1009
32. Li, M.; O'Doherty, G. A. Tetrahedron Lett. 2004, 45, 6407-6411
33. Babu, R. S.; O'Doherty, G. A. J. Carbohydr. Chem. 2005, 24, 169-177
34. Li, M.; Scott, J. G.; O'Doherty, G. A. Tetrahedron Lett. 2004, 45, 1005-1009
35. Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2002, 4, 1771-1774
36. Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226-2227
37. Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2001, 3, 401-404
38. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973-1976
39. de Oliveira, R. N.; Cottier, L.; Sinou, D.; Srivastava, R. M. Tetrahedron 2005, 61, 8271-8281
40. Zhou, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 4339-4342
41. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492-4493
42. Myers, A. G.; Zheng, B. Tetrahedron Lett. 1996, 37, 4841-4844
43. Myers, A. G.; Zheng, B.; Movassaghi, M. J. Org. Chem. 1997, 62, 7507
44. Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2002, 4, 1771-1774
45. This compatibility with the macrocyclic ketone functionality is important as there are many ketone-containing macrolide aglycons which can be used with this methodology. See
46. Ma, Z.; Nemoto, P. A. Curr. Med. Chem. Anti-Infect. Agents 2002, 1, 15-34