Synthesis of naturally occurring cyclohexene rings using stereodirected intramolecular diels-alder reactions through asymmetric 1,3-dioxane tethering

European Journal of Organic Chemistry

Volumn , Issue 15, 2011, Pages 2789-2800

  Abdelkafi, Hajer ^a   Evanno, Laurent ^a   Deville, Alexandre ^a   Dubost, Lionel ^a   Chiaroni, Angèle ^b   Nay, Bastien ^a  

^a MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^b CNRS   (France)

Author keywords

Diastereoselectivity; Intramolecular Diels Alder reaction; Natural products; Template synthesis; Total synthesis

Indexed keywords

EID: 79955806393     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001678     Document Type: Article

References (70)

1. For the seminal publication on the Diels-Alder reaction, see:, O. Diels, K. Alder, Justus Liebigs Ann. Chem. 1928, 460, 98-122.
2. For leading reviews on IMDA reactions, see
3. G. Brieger, J. N. Bennet, Chem. Rev. 1980, 80, 63-97.
4. A. G. Fallis, Can. J. Chem. 1984, 62, 183-234.
5. E. Ciganek, Org. React. 1984, 32, 1-374.
6. D. Craig, Chem. Soc. Rev. 1987, 16, 187-238.
7. W. R. Roush, in: Advances in cycloaddition, vol. 2 (Ed.:, D. P. Curran), JAI Press, Greenwich, 1990, pp. 91-146.
8. W. Oppolzer, in: Comprehensive Organic Synthesis, vol. 5 (Eds.:, B. M. Trost, I. Fleming), Pergamon, Oxford, UK, 1991, pp. 315-399.
9. W. R. Roush, in: Comprehensive Organic Synthesis, vol. 5 (Eds.:, B. M. Trost, I. Fleming), Pergamon, Oxford, UK, 1991, pp. 513-550.
10. For a sample of some well-known total syntheses featuring a Diels-Alder reaction, see
11. For cortisone and cholesterol, see:, R. B. Woodward, F. Sondheimer, D. Taub, K. Heusler, W. M. McLamore, J. Am. Chem. Soc. 1952, 74, 4223-4251.
12. for reserpine, see:, R. B. Woodward, F. E. Bader, H. Bickel, A. J. Frey, R. W. Kierstead, Tetrahedron 1958, 2, 1-57.
13. for anthracyclines, see:, A. S. Kende, Y. G. Tsay, J. E. Mills, J. Am. Chem. Soc. 1976, 98, 1967-1969.
14. for anthracyclines, see:, W. W. Lee, A. P. Martinez, T. H. Smith, D. W. Henry, J. Org. Chem. 1976, 41, 2296-2303.
15. for dynemicin A:, M. D. Shair, T. Y. Yoon, K. K. Mosny, T. C. Chou, S. J. Danishevsky, J. Am. Chem. Soc. 1996, 118, 9509-9525.
16. for FR182877, see:, C. D. Vanderwal, D. A. Vosburg, S. Weiler, E. J. Sorensen, J. Am. Chem. Soc. 2003, 125, 5393-5407.
17. K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. Int. Ed. 2002, 41, 1668-1698.
18. K. Takao, R. Munakata, K. Tadano, Chem. Rev. 2005, 105, 4779-4807.
19. M. Juhl, D. Tanner, Chem. Soc. Rev. 2009, 38, 2983-2992.
20. J. Poulin, C. M. Grisé-Bard, L. Barriault, Chem. Soc. Rev. 2009, 38, 3092-3101.
21. J. G. Buta, J. L. Flippen, W. R. Lusby, J. Org. Chem. 1978, 43, 1002-1003.
22. H. He, H. Y. Yang, R. Bigelis, E. G. H. Solum, M. Greenstein, G. T. Carter, Tetrahedron Lett. 2002, 43, 1633-1636.
23. M. Isaka, N. Rugseree, P. Maithip, P. Kongsaeree, S. Prabpai, Y. Thebtaranonth, Tetrahedron 2005, 61, 5577-5583.
24. S. M. Martin, S. A. Williamson, R. P. Gist, K. M. Smith, J. Org. Chem. 1983, 48, 5170-5180.
25. T.-C. Wu, K. N. Houk, Tetrahedron Lett. 1985, 26, 2293-2296.
26. R. Zschiesche, E. L. Grimm, H.-U. Reissig, Angew. Chem. Int. Ed. Engl. 1986, 25, 1086-1087.
27. R. Zschiesche, B. Frey, E. Grimm, H.-U. Reissig, Chem. Ber. 1990, 123, 363-374.
28. D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. Int. Ed. Engl. 1997, 36, 2119-2121.
29. P. Kim, M. H. Nantz, M. J. Kurth, M. M. Olmstead, Org. Lett. 2000, 2, 1831-1834.
30. M. E. Jung, A. Huang, T. W. Johnson, Org. Lett. 2000, 2, 1835-1837.
31. J. Wang, R. P. Hsung, S. K. Ghosh, Org. Lett. 2004, 6, 1939-1942.
32. E. L. Pearson, L. C. H. Kwan, C. I. Turner, G. A. Jones, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn, J. Org. Chem. 2006, 71, 6099-6109.
33. H. Yanai, H. Ogura, T. Taguchi, Org. Biomol. Chem. 2009, 7, 3657-3659.
34. E. L. Pearson, N. Kanizaj, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn, Chem. Eur. J. 2010, 16, 8280-8284.
35. M. Fengler-Veith, O. Schwardt, U. Kautz, B. Krämer, V. Jäger, Org. Synth. 2002, 78.
36. M. Fengler-Veith, O. Schwardt, U. Kautz, B. Krämer, V. Jäger, Org. Synth., Coll. Vol. 2004, 10, 405.
37. A. Mukhopadhyay, S. M. Ali, M. Husain, S. N. Suryawanshi, D. S. Bhakuni, Tetrahedron Lett. 1989, 30, 1853-1856.
38. D. S. Bakhuni, Pure Appl. Chem. 1990, 62, 1389-1392.
39. Carbohydrate-derived Diels-Alder partners have often been used in organic synthesis, see for instance
40. R. W. Franck, T. V. John, J. Org. Chem. 1983, 48, 3269-3276.
41. M. A. Rahman, B. Fraser-Reid, J. Am. Chem. Soc. 1985, 107, 5576-5578.
42. R. M. Giuliano, J. H. Buzby, N. Marcopulos, J. Org. Chem. 1990, 55, 3555-3562.
43. M. J. Lilly, M. S. Sherburn, Chem. Commun. 1997, 967-968.
44. L. Evanno, A. Deville, L. Dubost, A. Chiaroni, B. Bodo, B. Nay, Tetrahedron Lett. 2007, 48, 2893-2996.
45. M. J. Alves, V. C. M. Duarte, H. Faustino, A. G. Fortes, Tetrahedron: Asymmetry 2010, 21, 1817-1820.
46. S. Yamazaki, H. Kumagai, T. Takada, S. Yamabe, J. Org. Chem. 1997, 62, 2968-2974.
47. The stereochemistry of cycloadducts 38a and 38b was determined by NOESY experiments, which unambiguously showed transannular H-H correlations in the lactone ring. This was confirmed later by X-ray structure analysis of analogous derivatives 47a and 47b.
48. For some examples of Diels-Alder reactions involving Z-dienes, see
49. H. O. House, T. H. Cronin, J. Org. Chem. 1965, 30, 1061-1070.
50. R. F. Borch, A. J. Evans, J. J. Wade, J. Am. Chem. Soc. 1975, 97, 6282-6284.
51. S. G. Pyne, M. J. Hensel, S. R. Byrn, A. T. McKenzie, P. L. Fuchs, J. Am. Chem. Soc. 1980, 102, 5962-5964.
52. R. K. Boeckman Jr, T. R. Alessi, J. Am. Chem. Soc. 1982, 104, 3216-3217.
53. S. G. Pyne, M. J. Hensel, P. L. Fuchs, J. Am. Chem. Soc. 1982, 104, 5719-5728.
54. M. Yoshioka, H. Hakai, M. Ohno, J. Am. Chem. Soc. 1984, 106, 1133-1135.
55. S. Wattanasin, F. G. Kathawala, R. K. Boeckman Jr, J. Org. Chem. 1985, 50, 3810-3815.
56. R. Munakata, T. Ueki, H. Katakai, K. Takao, K. Tadano, Org. Lett. 2001, 3, 3029-3032.
57. T. J. Heckrodt, J. Mulzer, J. Am. Chem. Soc. 2003, 125, 4680-4681.
58. T. A. Dineen, W. R. Roush, Org. Lett. 2003, 5, 4725-4728.
59. T. A. Dineen, W. R. Roush, Org. Lett. 2004, 6, 2043-2046.
60. R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2004, 126, 11254-11267.
61. L. Evanno, A. Jossang, J. Nguyen-Pouplin, D. Delaroche, M. Seuleiman, B. Bodo, B. Nay, Planta Medica 2008, 870-872.
62. CCDC-631622 (for 47b), -CCDC-631623 (for 50), and -CCDC-631621 (for α- 52) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
63. The absolute stereochemistry of pyrrocidines has not yet been demonstrated.
64. H. Oikawa, J. Org. Chem. 2003, 68, 3552-3557.
65. For a study on the total synthesis of GKK1032 compounds involving an IMDA reaction, see:, M. Asano, M. Inoue, T. Katoh, Synlett 2005, 1539-1542.
66. For a study on the total synthesis of hirsutellones involving an IMDA reaction, see:, S. D. Tilley, K. P. Reber, E. J. Sorensen, Org. Lett. 2009, 11, 701-703.
67. Typically, a [1,5]-sigmatropic hydrogen shift from 1,3-pentadienes is expected to occur at 250-300 °C, see
68. W. R. Roth, J. König, Justus Liebigs Ann. Chem. 1966, 699, 24-32.
69. W. R. Roth, J. König, Justus Liebigs Ann. Chem. 1966, 699, 24-32.
70. W. R. Roth, J. König, K. Stein, Chem. Ber. 1970, 103, 426-439.