Convergent, fit-for-purpose, kilogram-scale synthesis of a 5-lipoxygenase inhibitor

Organic Process Research and Development

Volumn 16, Issue 2, 2012, Pages 214-219

  Ouellet, Stéphane G ^a   Gauvreau, Danny ^a   Cameron, Mark ^b   Dolman, Sarah ^a   Campeau, Louis Charles ^a   Hughes, Gregory ^a   O'Shea, Paul D ^a   Davies, Ian W ^b  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LINEAR SEQUENCE; PECHMANN CONDENSATION; REGIO-SELECTIVE; RESEARCH AND DEVELOPMENT; SYNTHETIC ROUTES;

ACETYLENE;

EID: 84857592084     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200299p     Document Type: Article

References (26)

1. Samuelsson, B. Science 1983, 220, 568
2. O'Byrne, P. M.; Israel, E.; Drazen, J. M. Ann. Intern. Med. 1997, 127, 472
3. Peters-Golden, M.; Henderson, W. R., Jr. N. Engl. J. Med. 2007, 357, 1841
4. Dwyer, J. H.; Allayee, H.; Dwyer, K. M.; Fan, J.; Wu, H.; Mar, R.; Lusis, A. J.; Mehrabian, M. N. Engl. J. Med. 2004, 350, 29
5. Grimm, E. L.; Ducharme, Y.; Frenette, R.; Friesen, R.; Gagnon, M.; Juteau, H.; Laliberte, S.; Mackay, B.; Gareau, Y. U.S. Pat. Appl. Publ. U.S. 2008/0188521, 2008.
6. Paul, S.; Gupta, M. Synthesis 2004, 1789
7. Commarieu, A.; Hoelderich, W.; Laffitte, J. A.; Dupont, M.-P. J. Mol. Cat. A.: Chem. 2002, 182-183, 137
8. Brooks, D. W.; Lu, L. D.-L.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1979, 18, 72
9. Masamune, S. Aldrichimica Acta 1978, 11, 23
10. von Pechmann, H.; Duisberg, C. Ber. Dtsch. Chem. Ges. 1883, 16, 2119
11. von Pechmann, H. Ber. Dtsch. Chem. Ges. 1884, 17, 929
12. For a recent example, see: Karimi, B.; Zareyee, D. Org. Lett. 2008, 10, 3989
13. Gosselin, F.; Britton, R. A.; Davies, I. W.; Dolman, S. J.; Gauvreau, D.; Hoerrner, R. S.; Hughes, G.; Janey., J.; Lau, S.; Molinaro, C.; Nadeau, C.; O'Shea, P. D.; Palucki, M.; Sidler, R. J. Org. Chem. 2010, 75, 4154
14. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
15. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
16. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249
17. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952
18. Li, L.; Zhang, G.; Zhu, A.; Zhang, L. J. Org. Chem. 2008, 73, 3630
19. Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081
20. Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005, 127, 16046
21. Yoo, E. J.; Ahlquist, M.; Bae, I.; Sharpless, B. K.; Fokin, V. V.; Chang, S. J. Org. Chem. 2008, 73, 5520
22. Brown, D. J.; Harper, J. S. J. Chem. Soc. 1963, 1276
23. Perrin, D. D. J. Chem. Soc. 1963, 1284
24. Katritzky, A. R.; Ji, F. B.; Fan, W.-Q.; Gallos, J. K.; Greenhill, J. V.; King, R. W.; Steel, P. J. J. Org. Chem. 1992, 57, 190
25. Sako, M.; Kawada, H. J. Org. Chem. 2004, 69, 8148
26. Huang, X.; O'Brien, E.; Thai, F.; Cooper, G. Org. Process Res. Dev. 2010, 14, 592