Intramolecular [1 + 4 + 1] cycloaddition: Establishment of the method

Journal of the American Chemical Society

Volumn 132, Issue 32, 2010, Pages 11179-11182

  Taber, Douglass F ^a   Guo, Pengfei ^a   Guo, Na ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[4 + 2] CYCLOADDITION; ABSOLUTE CONFIGURATION; CARBOCYCLIC RINGS; DIELS-ALDER; DIELS-ALDER CYCLOADDITIONS; DIENOPHILES; NATURAL PRODUCTS; POLYCYCLIC RING SYSTEMS; STEREOGENIC CENTERS;

KETONES; OLEFINS;

CYCLOADDITION;

KETONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION;

ALKENES; CYCLIZATION; CYCLOPROPANES; KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 77955584381     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103551x     Document Type: Article

References (65)

1. For an overview of synthetic strategies for polycarbocyclic natural products, see
2. Taber, D. F., Sheth, R. B., and Tian, W. J. Org. Chem. 2009, 74, 2433
3. For more recent examples, see
4. Chandler, C. L. and List, B. J. Am. Chem. Soc. 2008, 130, 6737
5. Surendra, K. and Corey, E. J. J. Am. Chem. Soc. 2008, 130, 8865
6. Trost, B. M., Ferreira, E. M., and Gutierrez, A. C. J. Am. Chem. Soc. 2008, 130, 16176
7. Pardeshi, S. G. and Ward, D. E. J. Org. Chem. 2008, 73, 1071
8. Li, L., McDonald, R., and West, F. G. Org. Lett. 2008, 10, 3733
9. Sethofer, S. G., Staben, S. T., Hung, O. Y., and Toste, F. D. Org. Lett. 2008, 10, 4315
10. Maity, P. and Lepore, S. D. J. Am. Chem. Soc. 2009, 131, 4196
11. Chung, W. K., Lam, S. K., Lo, B., Liu, L. L., Wong, W.-T., and Chiu, P. J. Am. Chem. Soc. 2009, 131, 4556
12. For a previous example of intramolecular cyclopropanation followed by Fe-mediated cyclocarbonylation, see ref 1a.
13. Crimmins, M. T. and Brown, B. H. J. Am. Chem. Soc. 2004, 10264-10266
14. Vosburg, D. A., Vanderwal, C. D., and Sorensen, E. J. J. Am. Chem. Soc. 2002, 4552-4553
15. Taber, D. F., Nakajima, K., Xu, M., and Rheingold, A. L. J. Org. Chem. 2002, 4501-4504
16. Johnson, T. W. and Corey, E. J. J. Am. Chem. Soc. 2001, 4475-4479
17. Boger, D. L., Ichikawa, S., and Jiang, H. J. Am. Chem. Soc. 2000, 12169-12173
18. Roush, W. R. and Sciotti, R. J. J. Am. Chem. Soc. 1998, 7411-7419
19. Taber, D. F. and Gunn, B. P. J. Am. Chem. Soc. 1979, 3992
20. Taber, D. F. and Saleh, S. A. J. Am. Chem. Soc. 1980, 5085
21. Takao, K., Munakata, R., and Tadano, K. Chem. Rev. 2005, 4779-4807
22. Craig, D. Chem. Soc. Rev. 1987, 187-238
23. Taber, D. F. and Guo, P. J. Org. Chem. 2008, 73, 9479
24. For earlier accounts of this sort of cyclization, see
25. Padwa, A. and Ku, H. J. Org. Chem. 1980, 45, 3756
26. Brinker, U. H., Schrievers, T., and Xu, L. J. Am. Chem. Soc. 1990, 112, 8609
27. Ashby, E. C., Park, B., Patil, G. S., Gadru, K., and Gurumurthy, R. J. Org. Chem. 1993, 58, 424
28. Jung, M. E. and Huang, A. Org. Lett. 2000, 2, 2659
29. For the preparation of the precursor diene iodides, see Miller, C. A. and Batey, R. A. Org. Lett. 2004, 699
30. Page, P. C. B., Vahedi, H., Batchelor, K. J., Hindley, S. J., Edgar, M., and Beswick, P. Synlett 2003, 1022
31. Wang, I., Dobson, G. R., and Jones, P. R. Organometallics 1990, 9, 2510
32. Taber, D. F. and Saleh, S. A. J. Am. Chem. Soc. 1980, 102, 5085
33. Elias, C. A. and Mihou, A. P. Tetrahedron Lett. 1999, 4861
34. For the development of Fe-mediated cyclocarbonylation, see
35. Victor, R., Ben-Shoshan, R., and Sarel, S. J. Org. Chem. 1978, 43, 4971
36. Taber, D. F., Kanai, K., Jiang, Q., and Bui, G. J. Am. Chem. Soc. 2000, 122, 6807
37. Taber, D. F., Bui, G., and Chen, B. J. Org. Chem. 2001, 66, 3423
38. Taber, D. F., Joshi, P. V., and Kanai, K. J. Org. Chem. 2004, 69, 2268
39. Taber, D. F. and Sheth, R. B. J. Org. Chem. 2008, 73, 8030
40. Frisch, M. J.; et al. Gaussian 03, Revision B03; Gaussian, Inc.: Pittsburgh, PA, 2003.
41. Chatterjee, N., Pandit, P., Halder, S., Patra, A., and Maiti, D. K. J. Org. Chem. 2008, 73, 7775-7778
42. For the diastereoselective allylation of 21, see Frater, G., Muller, U., and Guunther, W. Tetrahedron 1983, 40, 1269
43. Rubin, M., Rubina, M., and Gevorgyan, V. Chem. Rev. 2007, 3117-3179
44. Slaun, J. Chem. Rev. 2005, 396
45. Baldwin, J. E. Chem. Rev. 2003, 1197-1212
46. Sarel, S. Acc. Chem. Res. 1978, 204-211
47. Trost, B. M., Shen, H. C., Horne, D. B., Toste, F. D., Steinmetz, B. G., and Koradin, C. Chem.-Eur. J. 2005, 11, 2577
48. de Meijere, A. and Kurahashi, T. Synlett 2005, 2619
49. Liu, P., Cheong, P. H., Yu, Z. X., Wender, P. A., and Houk, K. N. Angew. Chem., Int. Ed. 2008, 3939-3941
50. Yu, Z. X., Cheong, P. H., Liu, P., Legault, C., Wender, P. A., and Houk, K. N. J. Am. Chem. Soc. 2008, 2378-2379
51. Wender, P. A., Haustedt, L. O., Lim, J., Love, J. A., Williams, T. J., and Yoon, J. Y. J. Am. Chem. Soc. 2006, 6302-6303
52. Wegner, H. A., de Meijere, A., and Wender, P. A. J. Am. Chem. Soc. 2005, 6530-6531
53. Wender, P. A., Gamber, G. G., Hubbard, R. D., Pham, S. M., and Zhang, L. J. Am. Chem. Soc. 2005, 2836-2837
54. Wender, P. A., Yu, Z., and Houk, K. N. J. Am. Chem. Soc. 2004, 9154-9155
55. Wender, P. A. and Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550-4553
56. Wender, P. A., Barzilay, C. M., and Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179-180
57. Wender, P. A. and Zhang, L. Org. Lett. 2000, 2, 2323-2326
58. Wender, P. A. and Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092
59. Wender, P. A., Fuji, M., Husfeld, C. O., and Love, J. A. Org. Lett. 1999, 1, 137-139
60. Wender, P. A., Glorius, F., Husfeld, C. O., Langkopf, E., and Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349
61. Wender, P. A., Husfeld, C. O., Langkopf, E., and Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941
62. Wender, P. A. and Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165
63. Wender, P. A., Takahashi, H., and Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721
64. Barluenga, J., Lopez, S., Trabanco, A. A., Fernandez-Acebes, A., and Florz, J. J. Am. Chem. Soc. 2000, 8145-8154
65. Sarpong, R., Su, J. T., and Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 13624-13625