A new approach to the synthesis of peptidomimetic renin inhibitors: Palladium-catalyzed asymmetric allylation of acyclic alkyl aryl ketones

Organic Letters

Volumn 14, Issue 12, 2012, Pages 3222-3225

  Hanessian, Stephen ^a   Chénard, Etienne ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; PALLADIUM; PROTEINASE INHIBITOR; RENIN;

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

ALKYLATION; CATALYSIS; KETONES; MOLECULAR STRUCTURE; PALLADIUM; PROTEASE INHIBITORS; RENIN; STEREOISOMERISM;

EID: 84862532285     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301332f     Document Type: Article

References (50)

1. Brewster, U. C.; Perazella, M. A. Am. J. Med. 2004, 116, 263
2. Weir, M. R.; Dzau, V. J. Am. J. Hypertens. 1999, 12, 205S
3. Weber, M. A. Am. J. Hypertens. 1999, 12, 189S
4. MacGregor, G. A.; Markandu, N. D.; Roulston, J. E.; Jones, J. C.; Morton, J. J. Nature 1981, 291, 329
5. For recent reviews, see: Maibaum, J.; Feldman, D. L. Annu. Rep. Med. Chem. 2009, 44, 105
6. Jensen, C.; Herold, P.; Brunner, H. R. Nat. Rev. Drug Discovery 2008, 7, 399
7. Siragy, H. M.; Kar, S.; Kirkpatrick, P. Nat. Rev. Drug Discovery 2007, 6, 779
8. Rahuel, J.; Rasetti, V.; Maibaum, J.; Rüeger, H.; Göschke, R.; Cohen, N.-C.; Stutz, S.; Cumin, F.; Fuhrer, W.; Wood, J. M.; Gruetter, M. G. Chem. Biol. 2000, 7, 493
9. Rahuel, J.; Priestle, J. P.; Gruetter, M. G. J. Struct. Biol. 1991, 107, 227
10. Maibaum, J.; Stutz, S.; Göschke, R.; Rigollier, P.; Yamaguchi, Y.; Cumin, F.; Rahuel, J.; Baum, H.-P.; Cohen, N.-C.; Schnell, C. R.; Fuhrer, W.; Gruetter, M. G.; Schilling, W.; Wood, J. M. J. Med. Chem. 2007, 50, 4832
11. Lindsay, K. B.; Skrydstrup, T. J. Org. Chem. 2006, 71, 4766
12. Dong, H.; Zhang, Z.-L.; Huang, J.-H.; Ma, R.; Chen, S.-H.; Li, G. Tetrahedron Lett. 2005, 46, 6337
13. Hanessian, S.; Claridge, S.; Johnstone, S. J. Org. Chem. 2002, 67, 4261
14. Dondoni, A.; De Lathauwer, G.; Perrone, D. Tetrahedron Lett. 2001, 42, 4819
15. Sandham, D. A.; Taylor, R. J.; Carey, J. S.; Fässler, A. Tetrahedron Lett. 2000, 41, 10091
16. Rüeger, H.; Stutz, S.; Göschke, R.; Spindler, F.; Maibaum, J. Tetrahedron Lett. 2000, 41, 10085
17. Satyanarayna Reddy, M.; Thirumalai Rajan, S.; Eswaraiah, S.; Venkat Reddy, G.; Rama Subba Reddy, K.; Sahadeva Reddy, M. WO 148392 A1, 2011.
18. Mickel, S. J.; Sedelmeier, G.; Hirt, H.; Schäfer, F.; Foulkes, M.; Prikoszich, W. WO 131304, 2006.
19. Herold, P.; Stutz, S. WO 0202500, 2002.
20. Herold, P.; Stutz, S. WO 0202487, 2002.
21. Herold, P.; Stutz, S.; Spindler, F. WO 0202508, 2002.
22. Hanessian, S.; Guesné, S.; Chénard, E. Org. Lett. 2010, 12, 1816
23. Minami, I.; Nisar, M.; Yuhara, M.; Shimizu, I.; Tsuji, J. Synthesis 1987, 992
24. See also: Tsuji, J. Palladium Reagents and Catalysts; Wiley: U.K., 2004.
25. Shimizu, I.; Yamada, T.; Tsuji, J. Tetrahedron Lett. 1980, 21, 3199
26. Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 6, 4387
27. For a recent review on metal catalyzed decarboxylative allylation, see: Weaver, J. D.; Recio, A., III; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846
28. Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044
29. Mohr, J. T.; Krout, M. R.; Stoltz, B. M. Nature 2008, 455, 323
30. Mohr, J. T.; Stoltz, B. M. Chem.-Asian J. 2007, 2, 1476
31. You, S.-L.; Dai, L.-X. Angew. Chem., Int. Ed. 2006, 45, 5246
32. Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 2846
33. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336 and references therein
34. Williams, J. M. J. Synlett 1996, 705
35. Bélanger, E.; Pouliot, M.-F.; Courtemanche, M.-A.; Paquin, J.-F. J. Org. Chem. 2012, 77, 317
36. McDougal, N. T.; Streuff, J.; Mukerjee, H.; Virgil, S. C.; Stoltz, B. M. Tetrahedron Lett. 2010, 51, 5550
37. Krout, M. R.; Mohr, J. T.; Stoltz, B. M. Org. Synth. 2009, 86, 181
38. Tani, K.; Behenna, D. C.; McFadden, R. M.; Stoltz, B. M. Org. Lett. 2007, 9, 2529
39. Liu, L.; Ma, H.; Fu, B. Molecules 2012, 17, 1992
40. Bayardon, J.; Sinou, D.; Guala, M.; Desimoni, G. Tetrahedron: Asymmetry 2004, 15, 3195 and references therein
41. Trost, B. M.; Xu, J.; Schmidt, T. J. Am. Chem. Soc. 2009, 131, 18343
42. For example, see: Behenna, D. C.; Stoltz, B. M.; Mohr, J. T.; Harned, A. M. U.S. 7,235,698, B2 2007.
43. Behenna, D. C.; Mohr, J. T.; Sherden, N. H.; Marinescu, S. C.; Harned, A. M.; Tani, K.; Seto, M.; Ma, S.; Novák, Z.; Krout, M. R.; McFadden, R. M.; Roizen, J. L.; Enquist, J. A., Jr.; White, D. E.; Levine, S. R.; Petrova, K. V.; Iwashita, A.; Virgil, S. C.; Stoltz, B. M. Chem.-Eur. J. 2011, 17, 14199
44. Kuwano, R.; Ishida, N.; Murakami, M. Chem. Commun. 2005, 3951
45. For the effect of an alkoxide in a related reaction, see: Trost, B. M.; Pissot-Soldermann, C.; Chen, I.; Schroeder, G. M. J. Am. Chem. Soc. 2004, 126, 4480
46. Sherden, N. H.; Behenna, D. C.; Virgil, S. C.; Stoltz, B. M. Angew. Chem., Int. Ed. 2009, 48, 6840
47. Keith, J. A.; Behenna, D. C.; Mohr, J. T.; Ma, S.; Marinescu, S. C.; Oxgaard, J.; Stoltz, B. M.; Goddard, W. A., III. J. Am. Chem. Soc. 2007, 129, 11876
48. Tsuji, J.; Sato, K.; Okumoto, H. J. Org. Chem. 1984, 49, 1341
49. Dowling, M. S.; Vanderwal, C. D. J. Am. Chem. Soc. 2009, 131, 15090
50. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vols. 1-3.