Efficient and scalable enantioselective synthesis of a CGRP antagonist

Organic Letters

Volumn 14, Issue 18, 2012, Pages 4938-4941

  Leahy, David K ^a   Fan, Yu ^a   Desai, Lopa V ^a   Chan, Collin ^a   Zhu, Jason ^a   Luo, Guanglin ^a   Chen, Ling ^a   Hanson, Ronald L ^a   Sugiyama, Masano ^a   Rosner, Thorsten ^a   Cuniere, Nicolas ^a   Guo, Zhiwei ^a   Hsiao, Yi ^a   Gao, Qi ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BMS 846372; BMS-846372; CALCITONIN GENE RELATED PEPTIDE; FUSED HETEROCYCLIC RINGS;

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

CALCITONIN GENE-RELATED PEPTIDE; CATALYSIS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84868254277     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302262q     Document Type: Article

References (21)

1. (a) Goadsby, P. J. Drugs 2005, 65, 2557.
2. (b) Edvinsson, L. Cephalalgia 2004, 24, 611.
3. (c) Williamson, D. J.; Hargreaves, R. J. Microsc. Res. Tech. 2001, 53, 167.
4. (d) Goadsby, P. J.; Edvinsson, L.; Ekman, R. Ann. Neurol. 1990, 28, 183.
5. (e) Goadsby, P. J.; Edvinsson, L. Ann. Neurol. 1993, 33, 48.
6. Bell, I. M.; Bednar, R. A.; Fay, J. F.; Gallicchio, S. N.; Hochman, J. H.; McMasters, D. R.; Miller-Stein, C.; Moore, E. L.; Mosser, S. D.; Pudvah, N. T.; Quigley,A. G.; Salvatore, C. A.; Stump, C. A.; Theberge, C. R.; Wong, B. K.; Zartman, C. B.; Zhang, X.-F.; Kane, S. A.; Graham, S. L.; Vacca, J. P.; Williams, T. M. Bioorg. Med. Chem. Lett. 2006, 16, 6165.
7. Goadsby, P. J.; Lipton, R. B.; Ferrari, M. D. N. Eng. J. Med. 2002, 346, 257.
8. Olesen, J.; Diener, H. C.; Husstedt, I. W.; Goadsby, P. J.; Hall, D.; Meier, U.; Pollentier, S.; Lesko, L. M. N. Eng. J. Med. 2004, 350, 1104.
9. Luo, G.; Chen, L.; Conway, C. M.; Denton, R.; Keavy, D.; Gulianello, M.; Huang, Y.; Kostich, W.; Lentz, K. A.; Mercer, S. E.; Schartman, R.; Signor, L.; Browning, M.; Macor, J. E.; Dubowchik, G. M. ACS Med. Chem. Lett. 2012, 3, 337.
10. Leahy, D. K.; Desai, L. V.; Deshpande, R. P; Mariadass, A. V.; Rangaswamy, S.; Rajagopal, S. K.; Madhavan, L.; Illenddula, S. J. Org. Process Res. Dev. 2012, 16, 224.
11. For a recent review of transition metal-catalyzed ketone arylations, see: Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082.
12. Jones, G.; Jones, R. K. J. Chem. Soc., Perkin. Trans. 1 1973, 27.
13. For a discussion of reactivity of the substituents on the pyridine ring, see:Uff, R. C. In Comprehensive Heterocyclic Chemistry: Katritzky, A., Ed.; Pergamon Press: Oxford, 1997; Vol VII, Chapter 2.06.
14. Tang, W.; Wang, W.; Chi, Y.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 3509.
15. (a) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
16. (b) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360.
17. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
18. Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447.
19. Holder, R. W.; Matturro, M. G. J. Org. Chem. 1977, 42, 2166.
20. Haubenstock, H.; Eliel, E. J. Am. Chem. Soc. 1962, 84, 2362.
21. Ashby, E. C.; Noding, S. A. J. Am. Chem. Soc. 1976, 98, 2010.