Enantioselective reductive coupling of alkynes and α-keto aldehydes via rhodium-catalyzed hydrogenation: An approach to bryostatin substructures

Organic Letters

Volumn 8, Issue 5, 2006, Pages 891-894

  Cho, Chang Woo ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; BRYOSTATIN; BRYOSTATIN 1; MACROLIDE; PYRAN DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKYNES; BRYOSTATINS; CATALYSIS; HYDROGENATION; MACROLIDES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRANS; RHODIUM; STEREOISOMERISM;

EID: 33644934506     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052976s     Document Type: Article

References (51)

1. Pettit, G. R.; Herald, C. L.; Doubek, D. L.; Herald, D. L.; Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1982, 104, 6846.
2. (a) Pettit, G. R. J. Nat. Prod. 1996, 59, 812.
3. (b) Lopanik, N.; Gustafson, K. R.; Lindquist, N. J. Nat. Prod. 2004, 67, 1412.
4. For reviews encompassing the biological properties of the bryostatins, see: (a) Kraft, A. S. J. Natl. Cancer Inst. 1993, 85, 1790.
5. (b) Petit, G. R. J. Nat. Prod. 1996, 59, 812.
6. Mutter, R.; Wills, M. Bioorg. Chem. Lett. 2000, 8, 1841.
7. Hale, K. J.; Hummersone, M., G.; Manaviazar, S.; Frigerio, M. Nat. Prod. Rep. 2002, 19, 413.
8. (e) Clamp, A.; Jayson, G. C. Anti-Cancer Drugs 2002, 13, 673.
9. (f) Kortmansky, J.; Schwartz, G. K. Cancer Invest. 2003, 21, 924.
10. (g) Hofmann, J. Curr. Cancer. Drug Targets 2004, 4, 125.
11. (h) Grant, S. Comb. Canc. Ther. 2005, 61.
12. (a) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354.
13. (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. J. Am. Chem. Soc. 1999, 121, 7540.
14. (a) Ohmori, K.; Ogawa, Y.; Obitsu, T.; Ishikawa, Y.; Nishiyama, S.; Yamamura, S. Angew. Chem., Int. Ed. 2000, 39, 2290.
15. (b) Ohmori, K. Bull. Chem. Soc. Jpn. 2004, 77, 875.
16. Kageyama, M.; Tamura, T.; Nantz, M.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7407.
17. Reviews: (a) Wender, P. A.; Martin-Cantalejo, Y.; Carpenter, A. J.; Chiu, A.; De Brabander, J.; Harran, P. G.; Jimenez, J.-M; Koehler, M. F. T.; Lippa, B.; Morrison, J. A.; Müller, S. G.; Müller, S. N.; Park, C.-M.; Shiozaki, M.; Siedenbiedel, C.; Skalitsky, D. J.; Tanaka, M.; Irie, K. Pure Appl. Chem. 1998, 70, 539.
18. (b) Wender, P. A.; Hinkle, K. W.; Koehler, M. F. T.; Lippa, B. Med. Res. Rev. 1999, 19, 388.
19. Wender, P. A.; Baryza, J. L.; Brenner, S. E.; Clarke, M. O.; Gamber, G. G.; Horan, J. C.; Jessop, T. C.; Kan, C.; Pattabiraman, K.; Williams. T. J. Pure Appl. Chem. 2003, 75, 143.
20. Keck, G. E.; Truong, A. P. Org. Lett. 2005, 7, 2153.
21. Review: Hale, K. J.; Hummersone, M. G.; Cai, J.; Manavaiazar, S.; Bhatia, G. S.; Lennon, J. A.; Frigerio, M.; Delisser, V. M.; Chumnongsaksarp, A.; Jogiya, N.; Lemaitre, A. Pure Appl. Chem. 2000, 72, 1659.
22. Review: Baron, A.; Ball, M.; Bradshaw, B.; Donnelly, S.; Germay, O.; Oller, P. C.; Kumar, N.; Martin, N.; O'Brien, M.; Omori, H.; Moore, C.; Thomas, E. J. Pure Appl. Chem. 2005, 77, 103.
23. (a) Lampe, T. F. J.; Hoffman, H. M. R. Chem. Commun. 1996, 1931.
24. (b) Lampe, T. F. J.; Hoffman, H. M. R. Tetrahedron Lett. 1996, 37, 7695.
25. Weiss, J.; Hoffman, H. M. R. Tetrahedron: Asymmetry 1997, 8, 3913.
26. Vakalopoulos, A.; Lampe, T. F. J.; Hoffman, H. M. R. Org. Lett. 2001, 3, 929.
27. (e) Seidel, M. C.; Smits, R.; Stark, C. B. W.; Frackenpohl, J.; Gaertzen, O.; Hoffman, H. M. R. Synthesis 2004, 1391.
28. (a) De Brabander, J.; Vanhessche, K.; Vandewalle, M. Tetrahedron Lett. 1991, 32, 2821.
29. (b) De Brabander, J.; Vandewalle, M. Synlett 1994, 231.
30. De Brabander, J.; Vandewalle, M. Synthesis 1994, 855.
31. De Brabander, J.; Kulkarni, A.; Garcia-Lopez, R.; Vandewalle, M. Tetrahedron: Asymmetry 1997, 8, 1721.
32. (a) Voight, E. A.; Seradj, H.; Roethle, P. A.; Burke, S. D. Org. Lett. 2004, 6, 4045.
33. (b) Voight, E. A.; Roethle, P. A.; Burke, S. D. J. Org. Chem. 2004, 69, 4534.
34. For hydrogen-mediated C-C bond formations developed in our laboratory, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
35. (b) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143.
36. Koech, P. K.; Krische, M. J. Org. Lett. 2004, 6, 691.
37. Marriner, G. A.; Garner. S. A.; Jang, H.-Y.; Krische, M. J. J. Org. Chem. 2004, 69, 1380.
38. (e) Jang, H.-Y.; Huddleston, R. R.; Krische, M. Angew. Chem., Int. Ed. 2003, 42, 4074.
39. (f) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664.
40. (g) Huddleston, R. R.; Jang, H.-Y. Krische, M. J. J. Am. Chem. Soc. 2003, 125, 11488.
41. (h) Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 7875.
42. Jang, H.-Y.; Hughes, F. W.; Gong, H.; Zhang, J.; Brodbelt, J. S.; Krische, M. J. Am. Chem. Soc. 2005, 127, 6174.
43. (j) Kong, J.-R.; Cho, C.-W.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 11269.
44. (k) Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
45. The α-keto aldehyde 2 was prepared via oxidation of the corresponding methyl ketone. See the Supporting Information for detailed experimental procedures.
46. (a) Brown, J. M.; Chaloner, P. A. J. Chem. Soc., Chem. Commun. 1980, 344.
47. (b) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Chem. Commun. 1983, 664.
48. Wender, P. A.; Baryza, J. L.; Bennett, C. E.; Bi, F. C.; Brenner, S. E.; Clarke, M. O.; Horan, J. C.; Kan, C.; Lacote, E.; Lippa, B.; Nell, P. G.; Turner, T. M. J. Am. Chem. Soc. 2002, 124, 13648.
49. Baxter, J.; Mata, E. G.; Thomas, E. J. Tetrahedron 1998, 54, 14359.
50. Trost, B. M.; Machacek, M. R.; Tsui, H. C. J. Am. Chem. Soc. 2005, 127, 7014.
51. Sakya, S. M.; Suarez-Contreras, M.; Dirlam, J. P.; O'Connell, T. N.; Hayashi, S. F.; Santoro, S. L.; Kamicker, B. J.; George, D. M.; Ziegler, C. B. Bioorg. Med. Chem. Lett. 2001, 11, 2751.