Concise, convergent syntheses of (±)-trichostatin a utilizing a Pd-catalyzed ketone enolate α-alkenylation reaction

Organic Letters

Volumn 13, Issue 14, 2011, Pages 3564-3567

  Cosner, Casey C ^a   Helquist, Paul ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID; KETONE; PALLADIUM; TRICHOSTATIC ACID; TRICHOSTATIN A; UNSATURATED FATTY ACID;

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

ALKENES; CATALYSIS; FATTY ACIDS, UNSATURATED; HISTONE DEACETYLASE INHIBITORS; HYDROXAMIC ACIDS; KETONES; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 79960184891     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200964m     Document Type: Article

References (53)

1. Johnstone, R. W. Nat. Rev. Drug Discovery 2002, 1, 287
2. Marks, P. A.; Rifkind, R. A.; Richon, V. M.; Breslow, R.; Miller, T.; Kelly, W. K. Nat. Rev. Cancer 2001, 1, 194
3. Wiech, N. L.; Fisher, J. F.; Helquist, P.; Wiest, O. Curr. Top. Med. Chem. 2009, 9, 257
4. Shuttleworth, S. J.; Bailey, S. G.; Townsend, P. A. Curr. Drug Targets 2010, 11, 1449
5. Halili, M. A.; Andrews, M. R.; Sweet, M. J.; Fairlie, D. P Curr. Top. Med. Chem. 2009, 9, 309
6. Andrews, K. T.; Tran, T. N.; Wheatley, N. C.; Fairlie, D. P. Curr. Top. Med. Chem. 2009, 9, 292
7. Echaniz-Laguna, A.; Bousiges, O.; Loeffler, J.-P.; Boutillier, A.-L. Curr. Med. Chem. 2008, 15, 1263
8. Kim, S.-J.; Lee, B.-H.; Lee, Y.-S.; Kang, K.-S. Biochem. Biophys. Res. Commun. 2007, 360, 593
9. Grant, S.; Easley, C.; Kirkpatrick, P. Nat. Rev. Drug Discovery 2007, 6, 21
10. Tsuji, N.; Kobayashi, M.; Nagashima, K.; Wakisaka, Y.; Koizumi, K. J. Antiobiot. 1976, 29, 1
11. Yoshida, M.; Kijima, M.; Akita, M.; Beppu, T. J. Biol. Chem. 1990, 265, 17174
12. Mishra, N.; Brown, D. R.; Olorenshaw, I. M.; Kammer, G. M. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 2628
13. Andrews, K. T.; Walduck, A.; Kelso, M. J.; Fairlie, D. P.; Saul, A.; Parsons, P. G. Int. J. Parasitol. 2000, 30, 761
14. Pipalia, N. H.; Cosner, C. C.; Huang, A.; Chatterjee, A.; Bourbon, P.; Farley, N.; Helquist, P.; Wiest, O.; Maxfield, F. R. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 5620
15. Cosner, C. C.; Markiewicz, J. T.; Bourbon, P.; Mariani, C. J.; Wiest, O.; Rujoi, M.; Rosenbaum, A. I.; Huang, A. Y.; Maxfield, F. R.; Helquist, P. J. Med. Chem. 2009, 52, 6494
16. Rosenbaum, A. I.; Cosner, C. C.; Mariani, C. J.; Maxfield, F. R.; Wiest, O.; Helquist, P. J. Med. Chem. 2010, 53, 5281
17. Fleming, I.; Iqbal, J.; Krebs, E. -P. Tetrahedron 1983, 39, 841
18. Mori, K.; Koseki, K. Tetrahedron 1988, 44, 6013
19. Zhang, S.; Duan, W.; Wang, W. Adv. Synth. Catal. 2006, 348, 1228
20. Markiewicz, J. T.; Schauer, D. J.; Löfstedt, J.; Corden, S. J.; Wiest, O.; Helquist, P. J. Org. Chem. 2010, 75, 2061
21. Chatterjee, A.; Richer, J.; Hulett, T.; Iska, V. B. R.; Wiest, O.; Helquist, P. Org. Lett. 2010, 12, 832
22. Piers, E.; Marais, P. J. Org. Chem. 1990, 55, 3454
23. Solè, D.; Peidŕ, E.; Bonjoch, J. Org. Lett. 2000, 2, 2225
24. Wang, T.; Cook, J. M. Org. Lett. 2000, 2, 2057
25. For examples of transition-metal-catalyzed intermolecular α-alkenylations, see: Fauvarque, J.; Jutand, A. J. Organomet. Chem. 1981, 209, 109
26. Chieffi, A.; Kamikawa, K.; Åhman, J.; Fox, J. M.; Buchwald, S. L. Org. Lett. 2001, 3, 1897
27. Huang, J.; Bunel, E.; Faul, M. M. Org. Lett. 2007, 9, 4343
28. Taylor, A. M.; Altman, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 9900
29. Hama, T.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 4976
30. Hama, T.; Liu, X.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 11176
31. Hlavinka, M. L.; Hagadorn, J. R. Organometallics 2007, 26, 4105
32. Hlavinka, M. L.; Hagadorn, J. R. Tetrahedron Lett. 2006, 47, 5049
33. Duez, S.; Bernhardt, S.; Heppekausen, J.; Fleming, F. F.; Knochel, P. Org. Lett. 2011, 13, 1690
34. Cosner, C. C.; Cabrera, P. J.; Byrd, K. M.; Thomas, A. M. A.; Helquist, P. Org. Lett. 2011, 13, 2071
35. Handa, M.; Scheidt, K. A.; Bossart, M.; Zheng, N.; Roush, W. R. J. Org. Chem. 2008, 73, 1031
36. Nicolaou, K. C.; Fylaktakidou, K. C.; Monenschein, H.; Li, Y.; Weyershausen, B.; Mitchell, H. J.; Wei, H.-X.; Guntupalli, P.; Hepworth, D.; Sugita, K. J. Am. Chem. Soc. 2003, 125, 15433
37. Vatèle, J.-M. Tetrahedron Lett. 2006, 47, 715
38. Apfel, C; Banner, D. W.; Bur, D.; Dietz, M.; Hirata, T.; Hubschwerlen, C.; Locher, H.; Page, M. G. P.; Pirson, W.; Rossé, G.; Specklin, J.-L. J. Med. Chem. 2000, 43, 2324
39. Paterson, I.; Woodrow, M. D.; Cowden, C. J. Tetrahedron Lett. 1998, 39, 6041
40. Bal, B. S.; Childers, W. E.; Pinnick, H. W. Tetrahedron 1981, 37, 2091
41. Dalcanale, E.; Montanari, F. J. Org. Chem. 1986, 51, 567
42. Lindren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888
43. Werle, S.; Fey, T.; Neudörfl, J. M.; Schmalz, H.-G. Org. Lett. 2007, 9, 3555
44. Lipshutz, B. H.; Lee, C.-T.; Servesko, J. M. Org. Lett. 2007, 9, 4713
45. Helquist, P. Applications of Zerovalent Nickel Complexes to Synthetic Organic Chemistry. Ph.D. Thesis, Cornell University, Ithaca, NY, January 1973.
46. Semmelhack, M. F.; Stauffer, R D.; Rogerson, T. D. Tetrahedron Lett. 1973, 14, 4519
47. Semmelhack, M. F.; Chong, B. P.; Stauffer, R D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507
48. Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833
49. Spielvogel, D. J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 3500
50. Matsubara, K.; Ueno, K.; Koga, Y.; Hara, K. J. Org. Chem. 2007, 72, 5069
51. Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195
52. Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676
53. Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082