Turning the corner: Recent advances in the synthesis of the welwitindolinones

Organic Preparations and Procedures International

Volumn 40, Issue 5, 2008, Pages 411-445

  Brown, Lauren E ^a   Konopelski, Joseph P ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

WELWITINDOLINONE;

EID: 55949136888     PISSN: 00304948     EISSN: None     Source Type: Journal    
DOI: 10.1080/00304940809458104     Document Type: Article

References (71)

1. K. Stratmann, R.E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith and T. A. Smitka, J. Am. Chem. Soc., 116, 9935 (1994).
2. J. I. Jimenez, U. Huber, R. E. Moore and G. M. L. Patterson, J. Nat. Prod., 62, 569 (1999).
3. a) C. D. Smith, J. T. Zilfou, K. Stratmann, G. M. L. Patterson and R. E. Moore, Mol. Pharm. 47, 241-247 (1995);
4. b) X. Zhang and C.D. Smith, Mol. Pharm., 49, 288 (1996).
5. J. P. Konopelski, H. Deng. K. Schiemann, J. M. Keane and M. M. Olmstead, Synlett, 1105 (1998).
6. J. L. Wood, A. A. Holubec, B. M. Stoltz, M. M. Weiss, J. A. Dixon, B. D. Doan, M. F. Shamji, J. M. Chen and T. P. Heffron, J. Am. Chem. Soc., 121, 6326 (1999).
7. C. Avendaño and J. C. Menéndez, Curr. Org. Synth., 1, 65 (2004).
8. J. Baudoux, A. J. Blake and N. S. Simpkins, Org. Lett., 7, 4087 (2005).
9. J. A. MacKay, R. L. Bishop and V. H. Rawal, Org. Lett., 7, 3421 (2005).
10. T. J. Greshock and R. L. Funk, Org. Lett., 8, 2643 (2006).
11. R. Lauchli and K. J. Shea, Org. Lett., 8, 5287 (2006).
12. P. S. Baran and J. M. Richter, J. Am. Chem. Soc., 127, 15394 (2005).
13. S. E. Reisman, J. M. Ready, A. Hasuoka, C. J. Smith and J. L. Wood, J. Am. Chem. Soc., 128, 1448 (2006).
14. J. Xia, L. E. Brown and J. P. Konopelski, J. Org. Chem., 72, 6885 (2007).
15. T. Kaudi, B. Quiclet-Sire, S. Seguin and S. Z. Zard, Angew Chem. Int. Ed., 39, 731 (2000).
16. M. E. Jung and F. Slowinski, Tetrahedron Lett., 42, 6835 (2001).
17. For a review on T2IMDA reactions and their use in the synthesis of bridgehead alkenes, see B. R. Bear, S. M. Sparks and K. J. Shea, Angew. Chem. Int. Ed., 40, 820 (2001).
18. M. P. Moyer, J. F. Shiurba and H. Rapoport, J. Org. Chem., 51, 5106 (1986).
19. M. Somei, K. Kizu, M. Kunimoto and F.Yamada, Chem. Pharm. Bull., 33, 3696 (1985).
20. a) K. Tonogaki and M. Mori, Tetrahedron Lett., 43, 2235 (2002);
21. b) S. T. Diver and A. J. Giessert Chem. Rev., 104, 1317 (2004).
22. K. J. Shea and S. Wise, Tetrahedron Lett., 20, 1011 (1979).
23. C. O. Kappe, S.S. Murphree and A. Padwa, Tetrahedron, 53, 14179 (1997).
24. J. M. Fox, X. Huang, A. Chieffi and S. L. Buchwald, J. Am. Chem. Soc., 122, 1360 (2000).
25. a) J. E. Appleton, K. N. Dack, A. D. Green and J. Steele, Tetrahedron Lett., 34, 1529 (1993);
26. b) A. Mahadevan, H. Sard, M. Gonzalez and J. C. McKew, Tetrahedron Lett., 44, 4589 (2003).
27. a) H. Muratake and M. Natsume, Tetrahedron, 46, 6331 (1990);
28. b) M. Sakagami, H. Muratake and M. Natsume, Chem. Pharm. Bull., 42, 1393 (1994).
29. L. N. Mander and S. P. Sethi, Tetrahedron Lett., 24, 5425 (1983).
30. J. McMurry, Org. React., 24, 187 (1976).
31. T. Shioiri, S. Yamada and K. Ninomiya, J. Am. Chem. Soc., 94, 6203 (1972).
32. T. J. Greshock and R.L. Funk, J. Am. Chem. Soc., 124, 754 (2002).
33. M. Polla and T. Fredj, Tetrahedron, 47, 5883 (1991).
34. T J. Greschock and R.L. Funk, J. Am. Chem. Soc., 128, 4946 (2006).
35. E. Tighineanu, F. Chiraleau and D. Raileanu, Tetrahedron, 36, 1385 (1980).
36. C. D. Gabbutt, J. D. Hepworth, B. M. Heron and S. L. Pugh, J. Chem. Soc. Perkin Trans. 1, 2799 (2002).
37. a) T. Ghaffar and A.W. Parkins, Tetrahedron Lett., 36, 8657 (1995);
38. b) T. Ghaffar and A. W. Parkins, J. Mol. Catal. A: Chem., 160, 249 (2000).
39. a) H. E. Baumgarten and A. Staklis, J. Am. Chem. Soc., 87, 1141 (1965);
40. b) H. E. Baumgarten, H. L. Smith and A. Staklis, J. Org. Chem., 40, 3554 (1975).
41. P. S. Baran, T. J. Maimone and J. M. Richter,Nature, 446, 404 (2007).
42. Upon our completion of this review, Wood and coworkers published a full paper further detailing the additional chemistry and numerous revisions in strategy that were required forthe successful total synthesis of 1. See S. E. Reisman, J. M. Ready, M. M. Weiss, A. Hasuoka, M. Hirata, K. Tamaki, T. V. Ovaska, C. J. Smith and J. L. Wood, J. Am. Chem. Soc., 130, 2087 (2008).
43. J. M. Ready, S. E. Reisman, M. Hirata, M. M. Weiss, K. Tamaki, T. Ovasaka and J. L. Wood, Angew. Chem. Int. Ed., 43, 1270 (2004).
44. B. M. Wang, Z. L. Song, C.A. Fan, Y. Q. Tu and W. M. Chen, Synlett, 10, 1497 (2003).
45. a) S. Atarashi, J. K. Choi, D. C. Ha, D. J. Hart, D. Kuzmich, C. S. Lee, S. Ramesh and S. C. Wu, J. Am. Chem. Soc., 119, 6226 (2000);
46. b) S. T. Hilton, T. C. T. Ho, G. Pljevaljcic and K. Jones, Org. Lett., 2, 2639 (2000).
47. A. Madlin and, L. E. Overman, Tetrahedron Lett., 33, 4859 (1992).
48. Y. H. Kim, H. S. Park and D.W. Kwon, Synth. Comm., 28, 4517 (1998).
49. F. Machrouhi, B. Hamann, J. L. Namy and H. B. Kagan, Synlett, 633 (1996).
50. J. Inanaga, M. Ishikawa and M. Yamaguchi, Chem. Lett., 1485 (1987).
51. R. S. Miller, J. M. Sealy, M. Shabangi, M. L. Kuhlman, J. R. Fuchs and R. A. Flowers, J. Am. Chem. Soc., 122, 7718 (2000).
52. Y. S. Liu, M. Z. Bei, Z. H. Zhou, K. Takaki and Y. Fujiwara, Chem. Lett., 1143 (1992).
53. M. L. Gross, D. H. Blank and W. M. Welch, J. Org. Chem., 58, 2104 (1993).
54. P. Soderman and G. Widmalm, Carbohydr. Res., 316, 184 (1999).
55. F. J. Moreno-Dorado, F. M. Guerra, F. L. Manzano, F. J. Aladro, Z.D. Jorge and G. M. Massanet, Tetrahedron Lett., 44, 6691 (2003).
56. A. S. Pilcher and P. Deshong, J. Org. Chem., 58, 5130 (1993).
57. D. A. Evans, K. T. Chapman and E. M. Carreira, J. Am. Chem. Soc., 110, 3560 (1988).
58. J. C. Martin and R. J. Arhart, J. Am. Chem. Soc., 93, 4327 (1971).
59. D. B. Dess and J. C. Martin, J. Org. Chem., 48, 4155 (1983).
60. D. Hoppe, Angew. Chem. Int. Ed. Engl., 13, 789 (1974).
61. G. E. Keck, T. T. Wager and S. F. McHardy, Tetrahedron, 55, 11755 (1999).
62. For further reviews of this accomplishment, see also a) J. A. Porco, Nature, 446, 383 (2007).
63. b) K. Gademann and S. Bonazzi, Angew. Chem. Int. Ed., 46, 5656 (2007).
64. 35 These two factors contribute to a single compound, numbered 10 in this review, appearing to have been given three different names over the course of several publications. Appendices A and B will attempt to clarify the inconsistencies.
65. P. S. Baran and J. M. Richter, J. Am. Chem. Soc., 126, 7450 (2004).
66. P. A. Wender, J. M. Erhardt and L. J. Letendre, J. Am. Chem. Soc., 103, 2114 (1981).
67. T. Fukuyama and X. Chen, J. Am. Chem. Soc., 116, 3125 (1994).
68. J. M. Richter, B. W .Whitefield, T. J. Maimone, D. W. Lin, M. P. Castroviejo and P. S. Baran, J. Am. Chem. Soc., 129, 12857 (2007).
69. T. Fukuyama and X. Chen, J. Am. Chem. Soc., 116, 3125 (1994).
70. When finalizing this document we discovered an additional article written by Menéndez that broadly reviews welwitindolinone synthetic efforts from isolation to present, including the achievements presented herein. See J. C. Menéndez, Top. Heterocycl. Chem., 11, 63 (2007).
71. R. E. Moore, C. Cheuk and G. M. L. Patterson,