Enantioselective synthesis of an HCV NS5a antagonist

Organic Letters

Volumn 16, Issue 9, 2014, Pages 2310-2313

  Mangion, Ian K ^a   Chen, Cheng Yi ^a   Li, Hongmei ^a   Maligres, Peter ^a   Chen, Yonggang ^a   Christensen, Melodie ^a   Cohen, Ryan ^a   Jeon, Ingyu ^a   Klapars, Artis ^a   Krska, Shane ^a   Nguyen, Hoa ^a   Reamer, Robert A ^a   Sherry, Benjamin D ^a   Zavialov, Ilia ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-(PYRROLIDIN-2-YL)-5-(2-(4-(5-(PYRROLIDIN-2-YL)-1H-IMIDAZOL-2-YL)PHENYL)BENZOFURAN-5-YL)-1H-IMIDAZOLE; 2 (PYRROLIDIN 2 YL) 5 (2 (4 (5 (PYRROLIDIN 2 YL) 1H IMIDAZOL 2 YL)PHENYL)BENZOFURAN 5 YL) 1H IMIDAZOLE; BENZOFURAN DERIVATIVE; IMIDAZOLE DERIVATIVE; IMINE; NS 5 PROTEIN, HEPATITIS C VIRUS; NS-5 PROTEIN, HEPATITIS C VIRUS; VIRUS PROTEIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

BENZOFURANS; HYDROGENATION; IMIDAZOLES; IMINES; MOLECULAR STRUCTURE; STEREOISOMERISM; VIRAL NONSTRUCTURAL PROTEINS;

EID: 84899826927     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500971c     Document Type: Article

References (40)

1. Kim, W. R. Microbes Infect. 2002, 4, 1219
2. Shepard, C. W.; Finelli, L.; Alter, M. J. Lancet Infect. Dis. 2005, 5, 558
3. Alter, M. J.; Kruszon-Moran, D.; Nainan, O. V.; McQuillan, G. M.; Gao, F.; Moyer, L. A.; Kaslow, R. A.; Margolis, H. S. N. Engl. J. Med. 1999, 341, 556
4. Hoofnagle, J. H.; Seeff, L. B. N. Engl. J. Med. 2006, 355, 2444
5. Pearlman, B. L. World J. Gastroenterol. 2008, 14, 3621
6. Asselah, T.; Benhamou, Y.; Marcellin, P. Liver Int. 2009, 29, 57
7. Pawlotsky, J. M. Gastroenterology 2011, 140, 746
8. Sheridan, C. Nat. Biotechnol. 2011, 29, 553
9. Vermehren, J.; Sarrazin, C. Eur. J. Med. Res. 2011, 16, 303
10. Gao, M.; Nettles, R. E.; Belema, M.; Snyder, L. B.; Nguyen, V. N.; Fridell, R. A.; Serrano-Wu, M. H.; Langley, D. R.; Sun, J. H.; O'Boyle, D. R.; Lemm, J. A.; Wang, C.; Knipe, J. O.; Chien, C.; Colonno, R. J.; Grasela, D. M.; Meanwell, N. A.; Hamann, L. G. Nature 2010, 465, 96
11. Lee, C. Arch. Pharm. Res. 2011, 34, 1403
12. Gao, M. Curr. Opin. Virol. 2013, 3, 514
13. Pol, S. Clin. Invest. 2013, 3, 191
14. Guedj, J.; Dahari, H.; Rong, L.; Sansone, N. D.; Nettles, R. E.; Cotler, S. J.; Layden, T. J.; Uprichard, S. L.; Perelson, A. S. Proc. Nat. Acad. Sci. U.S.A. 2013, 110, 3991
15. Coburn, C. A.; Meinke, P. T.; Chang, W.; Fandozzi, C. M.; Graham, D. J.; Hu, B.; Huang, Q.; Kargman, S.; Kozlowski, J.; Liu, R.; McCauley, J. A.; Nomeir, A. A.; Soll, R. M.; Vacca, J. P.; Wang, D.; Wu, H.; Zhong, B.; Olsen, D. B.; Ludmerer, S. W. ChemMedChem. 2013, 8, 1930
16. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307
17. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191-1223
18. Kozmin, S. A. Org. Lett. 2001, 3, 755
19. Clayden, J.; Vassiliou, N. Org. Biomol. Chem. 2006, 4, 2667
20. Kunz, R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240
21. Jeon, I.; Mangion, I. K. Synlett 2012, 23, 1927
22. Carpentier, J. F.; Bette, V. Curr. Org. Chem. 2002, 6, 913
23. Tang, W.; Zhang, X. Chem. Rev. 2003, 42, 5472
24. Hou, G.; Gosselin, F.; Li, W.; McWilliams, J. C.; Sun, Y.; Weisel, M.; O'Shea, P. D.; Chen, C.; Davies, I. W.; Zhang, X. J. Am. Chem. Soc. 2009, 131, 9882
25. Nguyen, T. B.; Bousserouel, H.; Wang, Q.; Guéritte, F. Org. Lett. 2010, 12, 4705
26. Nguyen, T. B.; Wang, Q.; Guéritte, F. Chem.-Eur. J. 2011, 17, 9576
27. Various dessicants were evaluated to suppress ketone formation without success. For a successful application of dessicants, see: Chi, Y.; Zhou, Y.-G.; Zhang, X. J. Org. Chem. 2003, 68, 4120
28. Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.; Armstrong, J. D.; Grabowski, E. J. J.; Tillyer, R. D.; Spindler, F.; Malan, C. J. Am. Chem. Soc. 2004, 126, 9918
29. Hansen, K. B.; Hsiao, Y.; Xu, F.; Rivera, N.; Clausen, A.; Kubryk, M.; Krska, S.; Rosner, T.; Simmons, B.; Balsells, J.; Ikemoto, N.; Sun, Y.; Spindler, F.; Malan, C.; Grabowski, E. J. J.; Armstrong, J. D. J. Am. Chem. Soc. 2009, 131, 8798
30. Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916
31. Kadyrov, R.; Riermeier, T. H. Angew.Chem., Int. Ed. 2003, 42, 5472
32. Boggs, S. D.; Cobb, J. D.; Gudmundsson, K. S.; Jones, L. A.; Matsuoka, R. T.; Millar, A.; Patterson, D. E.; Samano, V.; Trone, M. D.; Xie, S.; Zhou, X. Org. Process Res. Dev. 2007, 11, 539
33. Hayes, A. M.; Morris, D. J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2005, 127, 7318
34. Matharu, D. S.; Morris, D. J.; Kawamoto, A. M.; Clarkson, G. J.; Wills, M. Org. Lett. 2005, 7, 5489
35. Cheung, F. K.; Lin, C.; Minissi, F.; Lorente Crivillé, A.; Graham, M. A.; Fox, D. J.; Wills, M. Org. Lett. 2007, 9, 4659
36. Katkevics, M.; Kukosha, T.; Trufilkina, N. Synlett 2011, 17, 2525
37. Anderson, J. C.; Noble, A.; Tocher, D. A. J. Org. Chem. 2012, 77, 6703
38. Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447
39. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681
40. Crabtree, R. H. J. Chem. Soc., Dalton Trans. 2001, 2437