The intramolecular Diels-Alder strategy: Applications to total synthesis of natural products

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 60, Issue 7, 2002, Pages 679-690

  Suzuki, Yoshikazu ^a   Murata, Takeshi ^a   Takao, Ken Ichi ^a   Tadano, Kin Ichi ^a  

^a NONE

Author keywords

Endo exo selectivity; Intramolecular Diels Alder reaction; Natural product synthesis; Regioselectivity; Total synthesis; Type I triene; facial selectivity

Indexed keywords

ADDITION REACTIONS; MOLECULAR DYNAMICS; POLYCYCLIC AROMATIC HYDROCARBONS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DIELS-ALDER REACTION; INTRAMOLECULAR INVERSIONS;

OLEFINS;

EID: 0036659667     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.60.679     Document Type: Review

References (88)

1. W. R. Roush, In Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, L.A. Paquette Eds., Pergamon Press, Oxford, vol 5, pp. 513-550, (1991).
2. W.R. Roush, In Advances in Cycloaddition, D.P. Curran Ed., JAI Press, Greenwich, vol 2, pp 91-146, (1990).
3. A.G. Fallis, Acc. Chem. Res., 32, 464 (1999).
4. T.J. Brocksom, J. Nakamura, M.L. Ferreira, U. Brocksom, J. Braz. Chem. Soc., 12, 597 (2001).
5. C.O. Kappe, S.S. Murphree, A. Padwa, Tetrahedron, 53, 14179 (1997).
6. R. Hoffmann, R. B. Woodward, J. Am. Chem. Soc., 87, 4388 (1965).
7. D. Ginsburg, Tetrahedron, 39, 2095 (1983).
8. J. García, J. A. Mayoral, L. Salvatella, Acc. Chem. Res., 33, 658 (2000).
9. A. Arrieta, F. P. Cossío, B. Lecea, J. Org. Chem., 66, 6178 (2001).
10. T.-C. Wu, K. N. Houk, Tetrahedron Lett., 26, 2293, (1985).
11. F.K. Brown, K.N. Houk, ibid., 26, 2297 (1985).
12. T. Honda, H. Namiki, M. Kudoh, N. Watanabe, H. Nagase, H. Mizutani, Tetrahedron Lett., 41, 5927 (2000).
13. U.K. Bandarage, M.E. Kuehne, S.D. Glick, Tetrahedron, 55, 9405 (1999).
14. M.E. Kuehne, T.E. Wilson, U.K. Bandarage, W. Dai, Q. Yu, Tetrahedron, 57, 2085 (2001).
15. W.-C. Liu, C.-C. Liao, Chem. Commun., 1999, 117.
16. T.-H. Lee, C.-C. Liao, Tetrahedron Lett., 37, 6869 (1996).
17. R. Carlini, K. Higgs, C. Older, S. Randhawa, R. Rodrigo, J. Org. Chem., 62, 2330 (1997).
18. S.A. May, P.A. Grieco, H.-H. Lee, Synlett, 1997, 493.
19. P.A. Grieco, Y. Dai, J. Am. Chem. Soc., 120, 5128 (1998).
20. H.B. Kagan, O. Riant, Chem. Rev., 92, 1007 (1992).
21. H. Yamamoto, Lewis Acid Reagents, A Practical Approach: Oxford, 1999.
22. D.A. Evans, J.S. Johnson, J. Org. Chem., 62, 786 (1997).
23. S. Chackalamannil, R.J. Davies, Y. Wang, T. Asberom, D. Doller, J. Wong, D. Leone, J. Org. Chem., 64, 1932 (1999).
24. S. Chackalamannil, R. Davies, Org. Lett., 3, 1427 (2001).
25. J. Uenishi, R. Kawahama, O. Yonemitsu, J. Org. Chem., 62, 1691 (1997).
26. A.D. Brosius, L.E. Overman, L. Schwink, J. Am. Chem. Soc., 121,700 (1999).
27. H. Miyaoka, Y. Kajiwara, Y. Hara, Y. Yamada, J. Org. Chem., 66, 1429 (2001).
28. B. Delpech, D. Calvo, R. Lett, Tetrahedron Lett., 37, 1015 (1996).
29. M. Lee, I. Ikeda, T. Kawabe, S. Mort, K. Kanematsu, J. Org. Chem., 61, 3406 (1996).
30. A. Padwa, M. A. Brodney, M. Dimitroff, B. Liu, T. Wu, J. Org. Chem., 66, 3119 (2001).
31. A. Padwa, M. A. Brodney, S. M. Lynch, J. Org. Chem., 66, 1716 (2001).
32. M. Hatanaka, F. Ueno, I. Ueda, Tetrahedron Lett., 37, 89 (1996).
33. T.G. Back, V. O. Nava-Salgado, J.E. Payne, J. Org. Chem., 66, 4361 (2001).
34. V. Singh, S.Q. Alam, Chem. Commun., 1999, 2519.
35. S. Kuwahara, J. Ishikawa, W. S. Leal, S. Hamade, O. Kodama, Synthesis, 2000, 1930.
36. K.C. Nicolaou, D. Gray, J. Tae, Angew. Chem., Int. Ed., 40, 3679 (2001).
37. M. Kurosu, L.R. Marcin, T.J. Grinsteiner, Y. Kishi, J. Am. Chem. Soc., 120, 6627 (1998).
38. K. Yuki, M. Shindo, K. Shishido, Tetrahedron Lett., 42, 2517 (2001).
39. L.T. Burke, D.J. Dixon, S.V. Ley, F. Rodriguez, Org. Lett., 2, 3611 (2000).
40. K. Tatsuta, M. Itoh, R. Hirama, N. Araki, M. Kitagawa, Tetrahedron Lett., 38, 583 (1997).
41. Y. Suzuki, R. Nishimaki, M. Ishikawa, T. Murata, K. Takao, K. Tadano, Tetrahedon Lett., 40, 7835 (1999).
42. Y. Suzuki, R. Nishimaki, M. Ishikawa, T. Murata, K. Takao, K. Tadano, J. Org. Chem., 65, 8595 (2000).
43. J. Jauch, Synlett, 2001, 87.
44. G. Mehta, R. Uma, Acc. Chem. Res., 33, 278 (2000).
45. J.M. Coxon, R.D.J. Froese, B. Ganguly, A.P. Marchand, K. Morokuma, Synlett, 1999, 1681.
46. J.M. Coxon, D.Q. McDonald, Tetrahedron Lett., 33, 651 (1992).
47. M. Ishida, T. Aoyama, S. Kato, Chem. Lett., 1989, 663.
48. M. Ishida, Y. Beniya, S. Inagaki, S. Kato, J. Am. Chem. Soc., 112, 8980 (1990).
49. M. Ishida, T. Aoyama, Y. Beniya, S. Yamabe, S. Kato, S. Inagaki, Bull. Chem. Soc, Jpn., 66, 3430 (1993).
50. Y. Suzuki, A. Ohara, K. Sugaya, K. Takao, K. Tadano, Tetrahedon, 57, 7291 (2001).
51. J. Jauch, Eur. J. Org. Chem., 2001, 473.
52. J. Jauch, Angew. Chem., Int. Ed., 39, 2764 (2000).
53. A. Abad, C. Agulló, M. Arnó, A.C. Cunat, B. Meseguer, R.J. Zaragozá, J. Org. Chem., 63, 5100 (1998).
54. M. Arnó, M.A. González, R.J. Zaragozá; Tetrahedron, 55, 12419 (1999).
55. T.K.M. Shing, Q. Jian, J. Org. Chem., 65, 7059 (2000).
56. M. Toyota, Y. Nishikawa, K. Fukumoto, Tetrahedron, 52, 10347 (1996).
57. M. Toyota, T. Wada, K. Fukumoto, M. Ihara, J. Am. Chem. Soc., 120, 4916 (1998).
58. M. Toyota, M. Yokota, M. Ihara, Org. Lett., 1, 1627 (1999).
59. J. Schnaubelt, B. Frey, H.-U. Reissig, Helv. Chem. Acta, 82, 666 (1999).
60. B. Frey, J. Schnaubelt, H.-U. Reissig, Eur. J. Org. Chem., 1999, 1385.
61. W.R. Roush, M.L. Reilly, K. Koyama, B.B. Brown, J. Org. Chem., 62, 8708 (1997).
62. W.R. Roush, R.J. Sciotti, J. Am. Chem. Soc., 120, 7411 (1998).
63. O. Hoshino, M. Ishizaki, K. Kamei, M. Taguchi, T. Nagao, K. Iwaoka, S. Sawaki, B. Umezawa, Y. Iitaka, J. Chem. Soc., Perkin Trans. 1, 1996, 571.
64. K. Tadano, T. Murata, T. Kumagai, S. Ogawa, Tetraherdon Lett., 34, 7279 (1993).
65. T. Murata, T. Kumagai, M. Ishikawa, K. Tadano, S. Ogawa, Bull. Chem. Soc. Jpn., 69, 3551 (1996).
66. S.F. Martin, J.M. Humphrey, A. Ali, M.C. Hillier, J. Am. Chem. Soc., 121, 866 (1999).
67. D.J. Hart, J. Li, W.-L. Wu, A. P. Kozikowski, J. Org. Chem., 62, 5023 (1997).
68. S. Hofman, L.-J. Gao, H. V. Dingenen, N.G.C. Hosten, D.V. Haver, P.J. DeClercq, M. Milanesio, D. Viterbo, Eur. J. Org. Chem., 2001, 2851.
69. M.D. Shair, T.Y. Yoon, K.K. Mosny, T.C., Chou, S.J. Danishefsky, J. Am. Chem. Soc., 118, 9509 (1996).
70. J. Leonard, A.B. Hague, M.F. Jones, Tetrahedron Lett., 38, 3071 (1997).
71. S.M. Sparks, K.J. Shea, Tetrahedron Lett., 41, 6721 (2000).
72. P.A. Jacobi, Y. Li, J. Am. Chem. Soc., 123, 9307 (2001).
73. E.J. Bush, D.W. Jones, J. Chem. Soc., Perkin Trans. 1, 1997, 3531.
74. S. Doye, T. Hotopp, R. Wartchow, E. Winterfeldt, Chem. Eur. J., 4, 1480 (1998).
75. S. Sano, K. Mort, Eur. J. Org. Chem., 1999, 1679.
76. T. Tashiro, M. Bando, K. Mort, Synthesis, 2000, 1852.
77. E. Merifield, E.J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1999, 3269.
78. E.J. Thomas, J.P. Watts, ibid., 1999, 3285.
79. J.A. McCauley, K. Nagasawa, P.A. Lander, S.G. Mischke, M.A. Semones, Y. Kishi, J. Am. Chem. Soc., 120, 7647 (1998).