A Diels-Alder-based total synthesis of (-)-kainic acid

Journal of Organic Chemistry

Volumn 77, Issue 12, 2012, Pages 5286-5296

  Orellana, Arturo ^a   Pandey, Sushil K ^a   Carret, Sébastien ^a   Greene, Andrew E ^a   Poisson, Jean François ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYPROLINES; DIELS-ALDER CYCLOADDITIONS; EFFICIENT SYNTHESIS; KAINIC ACID; MALONATES; NATURAL PRODUCTS; STEREOCONTROL; TOTAL SYNTHESIS;

AMINO ACIDS;

CYCLOADDITION;

HYDROXYPROLINE; KAINIC ACID; MALONIC ACID; NATURAL PRODUCT; PYRROLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOMER; ESTERIFICATION; RACEMIZATION; STEREOCHEMISTRY; SYNTHESIS;

CYCLIZATION; HYDROXYPROLINE; KAINIC ACID; MALONATES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84862564460     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300608g     Document Type: Article

References (99)

1. Murakami, S.; Takemoto, T.; Shimizu, Z. J. Pharm. Soc. Jpn. 1953, 73, 1026-1028
2. (-)-Kainic acid has also been isolated from Centrocerus clavulatum: Impellizzeri, G.; Mangiafico, G.; Oriente, G.; Piattelli, M.; Sciuto, S.; Fattorusso, E.; Magno, S.; Santacroce, C.; Sica, D. Phytochemistry 1975, 14, 1549-1557
3. Balansard, G.; Pellegrini, M.; Cavalli, C.; Timon-David, P. Ann. Pharm. Fr. 1983, 41, 77-86.
4. Shortage of Kainic Acid Hampers Neuroscience Research. Chem. Eng. News 2000, 78 (1), 14-15.
5. Producers Strive to Bring Kainic Acid Back on the Market. Chem. Eng. News 2000, 78 (10), 31.
6. Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978
7. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem Soc., Chem. Commun. 1987, 1220
8. Takano, S.; Sugihara, T.; Satoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467
9. Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem Soc., Chem. Commun. 1988, 1204
10. Yoo, S.-E.; Lee, S.-H.; Yi, K.-Y.; Jeong, N. Tetrahedron Lett. 1990, 31, 6877
11. Baldwin, J. E.; Monoley, M. G.; Parsons, A. F. Tetrahedron 1990, 46, 7263
12. Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem Soc., Chem. Commun. 1991, 390
13. Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G. P.; Zanirato, V. J. Org. Chem. 1992, 57, 6279
14. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem Soc., Perkin Trans.1 1992, 553
15. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem Soc., Chem. Commun. 1992, 169
16. Yoo., S.-E.; Lee, S.-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435
17. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem Soc., Chem. Commun. 1993, 125
18. Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773
19. Yoo, S.-E.; Lee, S. H. J. Org. Chem. 1994, 59, 6968
20. Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418
21. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Synlett 1997, 275
22. Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857
23. Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896
24. Bachi, M. D.; Melman, A. Pure Appl. Chem. 1998, 70, 259
25. Cossy, J.; Cases, M.; Pardo, D. G. Synlett 1998, 507
26. Rubio, A.; Ezquerra, J.; Escribano, A.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron Lett. 1998, 39, 2171
27. Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139
28. Cossy, J.; Cases, M.; Pardo, D. G. Tetrahedron 1999, 55, 6153
29. Campbell, A. D.; Taylor, R. J. K.; Raynham, T. M. Chem Commun. 1999, 245
30. Nakagawa, H.; Sugahara, T.; Ogasawara, K. Org. Lett. 2000, 2, 3181
31. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199
32. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 3194
33. Hirasawa, H.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 7587
34. Xia, Qian; Ganem, B. Org. Lett. 2001, 3, 485
35. Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727
36. Clayden, J.; Menet, C. J.; Mansfield, D. J. Chem Commun. 2002, 38
37. Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467
38. Martinez, M. M.; Hoppe, D. Org. Lett. 2004, 6, 3743
39. Poisson, J.-F.; Orellana, A.; Greene, A. E. J. Org. Chem. 2005, 70, 10860
40. Anderson, J. C.; O'Loughlin, J. M. A.; Tornos, J. A. Org. Biomol. Chem. 2005, 3, 2741
41. Martínez, M. M.; Hoppe, D. Eur. J. Org. Chem. 2005, 1427
42. Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2005, 127, 4763
43. Scott, M. E.; Lautens, E. Org. Lett. 2005, 7, 3045
44. Morita, Y.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2005, 7, 4337
45. Hodgson, D. M.; Hachisu, S.; Andrews, M. D. Org. Lett. 2005, 7, 815
46. Pandey, S. K.; Orellana, A.; Greene, A. E.; Poisson, J.-F. Org. Lett. 2006, 8, 5665
47. Thuong, M. B. T.; Sottocornola, S.; Prestat, G.; Broggini, G.; Madec, D.; Poli, G. Synlett 2007, 1521
48. Sakaguchi, H.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2007, 9, 1635
49. Chalker, J. M.; Yang, A.; Deng, K.; Cohen, T. Org. Lett. 2007, 9, 3825
50. Jung, Y. C.; Yoon, C. H.; Turos, E.; Yoo, K. S.; Jung, K. W. J. Org. Chem. 2007, 72, 10114
51. Tomooka, K.; Akiyama, T.; Man, P.; Suzuki, M. Tetrahedron Lett. 2008, 49, 6327
52. Sakaguchi, H.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2008, 10, 1711
53. Farwick, A.; Helmchen, G. Org. Lett. 2010, 12, 1108
54. Kitamoto, K.; Sampei, M.; Nakayama, Y.; Sato, T.; Chida, N. Org. Lett. 2010, 12, 5756
55. Takita, S.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2011, 13, 2068
56. Lemière, G.; Sedehizadeh, S.; Toueg, J.; Fleary-Roberts, N.; Clayden, J. Chem. Commun. 2011, 47, 3745
57. Lowe, M. A.; Ostovar, M.; Ferrini, S.; Chen, C. C.; Lawrence, P. G.; Fontana, F.; Calabrese, A. A.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2011, 50, 6370
58. Wei, G.; Chalker, J. M.; Cohen, T. J. Org. Chem. 2011, 76, 7912
59. trans -4-Hydroxy-L-proline, however, has been employed for the synthesis of congeners. See: Remuzon, P. Tetrahedron 1996, 52, 13803-13835
60. Jenner, G. Tetrahedron 1997, 53, 2669-2695
61. Jenner, G. J. Phys. Org. Chem. 2002, 15, 1-13
62. Matsumoto, K.; Hamana, H.; Iida, H. Helv. Chim. Acta 2005, 88, 2033-2234
63. High Pressure Chemistry; van Eldik, R.; Kläner, F.-G., Eds.; John Wiley & Sons, Ltd.: Weinheim, 2002.
64. Dauben, W. G.; Kessel, C. R.; Takemura, K. H. J. Am. Chem. Soc. 1980, 102, 6893
65. Banwell, M. G.; Edwards, A. J.; Harfoot, G. J.; Jolliffe, K. A. J. Chem. Soc., Perkin Trans. 1 2002, 2439
66. Kienzler, M. A.; Suseno, S.; Trauner, D. J. Am. Chem. Soc. 2008, 130, 8604-8605
67. Waalboer, D. C. J.; Schaapman, M. C.; van Delft, F. L.; Rutjes, F. P. J. T. Angew. Chem., Int. Ed. 2008, 47, 6576-6578
68. Ballerini, E.; Minuti, L.; Piermatti, O.; Pizzo, F. J. Org. Chem. 2009, 74, 4311-4317
69. Suzuki, T.; Kobayashi, S. Org. Lett. 2010, 12, 2920-2923
70. Danishefsky, S.; Kitahara, T.; Yan, C. F.; Morris, J. J. Am. Chem. Soc. 1979, 101, 6996-7000
71. Jankowski, C. K.; LeClair, G.; Bélanger, J. M. R.; Paré, J. R. J.; VanCalsteren, M.-R. Can. J. Chem. 2001, 79, 1906-1909
72. Boger, D. L.; Patel, M. Tetrahedron Lett. 1986, 27, 683-686
73. Grieco, P. A.; Lis, R.; Zelle, R. E.; Finn, J. J. Am. Chem. Soc. 1986, 108, 5908-5919
74. O'Connor, P. D.; Mander, L. N.; McLachlan, M. M. W. Org. Lett. 2004, 6, 703-706
75. Paczkowski, R.; Maichle-Mössmer, C.; Maier, M. E. Org. Lett. 2000, 2, 3967-3969
76. Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561-1562
77. Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920-6930
78. Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992-9993
79. Sprott, K. T.; Corey, E. J. Org. Lett. 2003, 5, 2465-2467
80. Davies, H. M. L.; Dai, X. J. Am. Chem. Soc. 2004, 126, 2692-2693
81. Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 7843-7844
82. Rehnberg, N.; Sundin, A.; Magnusson, G. J. Org. Chem. 1990, 55, 5477-5483
83. Ponten, F.; Magnusson, G. J. Org. Chem. 1997, 62, 7978-7983
84. Chataigner, I.; Hess, E.; Toupet, L.; Piettre, S. R. Org. Lett. 2001, 3, 515-518
85. Chretien, A.; Chataigner, I.; L'Hélias, N.; Piettre, S. R. J. Org. Chem. 2003, 68, 7990-8002
86. Strunz, G. M.; Bethell, R.; Dumas, M. T.; Boyonoski, N. Can. J. Chem. 1997, 75, 742-753
87. Martin, C.; Mailliet, P.; Maddaluno, J. J. Org. Chem. 2001, 66, 3797-3805
88. Pichon, N.; Harrison-Marchand, A.; Mailliet, P.; Maddaluno, J. J. Org. Chem. 2004, 69, 7220-7227
89. Reddy, T. J.; Rawal, V. H. Org. Lett. 2000, 2, 2711-2712
90. Jung, M. E.; Davidov, P. Angew. Chem., Int. Ed. 2002, 41, 4125-4128
91. Jung, M. E.; Ho, D.; Chu, H. V. Org. Lett. 2005, 7, 1649-1651
92. Del Valle, J. R.; Goodman, M. J. Org. Chem. 2003, 68, 3923-3931 This compound is also commercially available
93. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639
94. Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727-4733
95. Attempts to form the olefins more directly from the alcohols by using Grieco's procedure were unsuccessful: Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485-1486
96. Honda, T.; Takahashi, R.; Namiki, H. J. Org. Chem. 2005, 70, 499-504
97. For an alternative preparation of this aldehyde (for a synthesis of domoic acid), see: Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511-3513
98. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302
99. For other examples, see: Pandey, S. K.; Greene, A. E.; Poisson, J.-F. J. Org. Chem. 2007, 72, 7769-7770