Stereocontrolled syntheses of kainoid amino acids from 7-azabicyclo[2.2.1] heptadienes using tandem radical addition-homoallylic radical rearrangement

Journal of Organic Chemistry

Volumn 70, Issue 22, 2005, Pages 8866-8876

  Hodgson, David M ^a   Hachisu, Shuji ^a   Andrews, Mark D ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBOXYLIC ACIDS; NITROGEN; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DRUG DEVELOPMENT; NEUROEXCITANTS; OXIDATIVE CLEAVAGE; STEREOCONTROLLED SYNTHESES;

AMINO ACIDS;

3 (CARBOXYMETHYL)PYRROLIDINE 2,4 DICARBOXYLIC ACID; 7 AZABICYCLO[2.2.1]HEPTADIENE; ALLYL COMPOUND; AMINO ACID; BICYCLO COMPOUND; HYDROGEN; IODIDE; KAINIC ACID DERIVATIVE; LACTONE DERIVATIVE; NITROGEN; PYRROLIDINE DERIVATIVE; RADICAL; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DEOXYGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

ALCOHOLS; ALKYLATION; AMINO ACIDS; AZA COMPOUNDS; CYCLIZATION; FREE RADICALS; HYDROGEN; IODINE; KAINIC ACID; LACTONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRROLIDINES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; SULFUR; TEMPERATURE;

EID: 27444441302     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0513865     Document Type: Article

References (72)

1. (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, pp 161-310.
2. (b) Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856.
3. (c) Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
4. (a) Hodgson, D. M.; Bebbington, M. W. P.; Willis, P. Chem. Commun. 2001, 889-890.
5. (b) Hodgson, D. M.; Bebbington, M. W. P.; Willis, P. Org. Biomol. Chem. 2003, 1, 3787-3798.
6. For other nitrogen-directed radical rearrangements, see: (a) Rigby, J. H.; Pigge, F. C. Tetrahedron Lett. 1996, 37, 2201-2204.
7. (b) Hodgson, D. M.; Galano, J.-M. Org. Lett. 2005, 7, 2221-2224.
8. Wayner, D. D. M.; Clark, K. B.; Rauk, A.; Yu, D.; Armstrong, D. A. J. Am. Chem. Soc. 1997, 119, 8925-8932.
9. (a) Hodgson, D. M.; Hachisu, S.; Andrews, M. D. Org. Lett. 2005, 7, 815-817.
10. (b) Hodgson, D. M.; Hachisu, S.; Andrews, M. D. Synlett 2005, 1267-1270.
11. (a) Parsons, A. F. Tetrahedron 1996, 52, 4149-4174.
12. (b) Moloney, M. G. Nat. Prod. Rep. 2002, 19, 597-616.
13. (c) Clayden, J.; Read, B.; Hebditch, K. R. Tetrahedron 2005, 61, 5713-5724.
14. (d) Calaf, R.; Barlatier, A.; Maillard, C.; Balansard, G.; Garcon, D. Plant. Med. Phytother. 1989, 23, 24-32.
15. (e) Calaf, R.; Barlatier, A.; Maillard, C.; Ollivier-Vidal, E.; Garcon, D. Plant. Med. Phytother. 1989, 23, 16-23.
16. Zaman, L.; Arakawa, O.; Shimosu, A.; Onoue, Y.; Nishio, S.; Shida, Y.; Noguchi, T. Toxicon 1997, 35, 205-212.
17. (a) Shinozaki, H.; Konishi, S. Brain Res. 1970, 24, 368-371.
18. (b) Olney, J. W.; Rhee, V.; Ho, O. L. Brain Res. 1974, 77, 507-512.
19. (c) Bleakman, D.; Lodge, D. Neuropharmacology 1998, 37, 1187-1204.
20. For selected recent syntheses, see: (a) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139-11143.
21. (b) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 3194-3204.
22. (c) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485-487.
23. (d) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727-4733.
24. (e) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2005, 127, 4763-4776.
25. (f) Martinez, M. M.; Hoppe, D. Eur. J. Org. Chem. 2005, 1427-1443.
26. (g) Scott, M. E.; Lautens, M. Org. Lett. 2005, 7, 3045-3047.
27. (h) Morita, Y.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2005, 7, 4337-4340.
28. Leung-Toung, R.; Liu, Y.; Muchowski, J. M.; Wu, Y.-L. J. Org. Chem. 1998, 63, 3235-3250.
29. Joung, M. J.; Ahn, J. H.; Lee, D. W.; Yoon, N. M. J. Org. Chem. 1998, 63, 2755-2757.
30. Newcomb, M.; Sanchez, R. M.; Kaplan, J. J. Am. Chem. Soc. 1987, 109, 1195-1199.
31. (a) Malpass, J. R.; White, R. J. Org. Chem. 2004, 69, 5328-5334.
32. (b) Malpass, J. R.; Handa, S.; White, R. Org. Lett. 2005, 7, 2759-2762.
33. (c) Hodgson, D. M.; Maxwell, C. R.; Wisedale, R.; Matthews, I. R.; Carpenter, K. J.; Dickenson, A. H.; Wonnacott, S. J. Chem. Soc., Perkin Trans, 1 2001, 3150-3158.
34. (a) Jin, Z.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 3022-3028.
35. (b) Hodgson, D. M.; Jones, M. L.; Maxwell, C. R.; Ichihara, O.; Matthews, I. R. Synlett 2005, 325-327.
36. (a) Chick, W. H.; Ong, S. H. Chem. Commun. 1969, 216-217.
37. (b) Humphrey, L. B.; Hodgson, B.; Pincock, R. E. Can. J. Chem. 1968, 46, 3099-3103.
38. Kawamura, T.; Koyama, T.; Yonezawa, T. J. Am. Chem. Soc. 1973, 95, 3220-3228.
39. Curran, D. P. Synthesis 1988, 417-439.
40. Mikami, S.; Fujita, K.; Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. Org. Lett. 2001, 3, 1853-1855.
41. Jang, D. O.; Cho, D. H.; Chung, C.-M. Synlett 2001, 1923-1924.
42. Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179-1193.
43. Najera, C.; Yus, M. Tetrahedron 1999, 55, 10547-10658.
44. Suh, Y.-G.; Jung, J.-K.; Seo, S.-Y.; Min, K.-H.; Shin, D.-Y.; Lee, Y.-S.; Kim, S.-H.; Park, H.-J. J. Org. Chem. 2002, 67, 4127-4137.
45. Goldberg, O.; Luini, A.; Teichberg, V. I. Tetrahedron Lett. 1980, 21, 2355-2358.
46. Arakawa, Y.; Yasuda, M.; Ohnishi, M.; Yoshifuji, S. Chem. Pharm. Bull. 1997, 45, 255-259.
47. Collins, P.; Ferrier, R. Monosaccharides: Their Chemistry and Their Roles in Natural Products; Wiley: Chichester, 1995; pp 126-127.
48. Marko, I. E.; Murphy, F.; Kumps, L.; Ates, A.; Touillaux, R.; Craig, D.; Carballares, S.; Dolan, S. Tetrahedron 2001, 57, 2609-2619.
49. Baldwin, J. E.; Turner, S. C. M.; Moloney, M. G. Synlett 1994, 925-928
50. Tsuji, J. Synthesis 1984, 369-384.
51. (a) Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron 1997, 53, 7577-7586.
52. (b) Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron 1997, 53, 10733-10742.
53. Goldberg, O.; Luini, A.; Teichberg, V. I. J. Med. Chem. 1983, 26, 39-42.
54. Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S.; Tomasini, C. J. Org. Chem. 1984, 49, 701-703.
55. (a) Baldwin, J. E.; Fryer, A. M.; Pritchard, G. J. J. Org. Chem. 2001, 66, 2588-2596.
56. (b) Ahern, D. G.; Seguin, R. J.; Filer, C. N. J. Labeled Compd. Radiopharm. 2002, 45, 401-405.
57. Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773-2778.
58. Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
59. (a) Wladislaw, B.; Marzorati, L.; Russo, V. F. T.; Zim, M. H.; Di Vitta, C. Tetrahedron Lett. 1995, 36, 8367-8370.
60. (b) Taylor, R. J. K.; Casy, G. Org. React. 2003, 62, 357-475.
61. (a) Laba, V. I.; Polievktov, M. K.; Prilezhaeva, E. N.; Mairanovskii, S. G. Izu. Akad. Nauk., Ser. Khim. 1969, 2149-2156;
62. Laba, V. I.; Polievktov, M. K.; Prilezhaeva, E. N.; Mairanovskii, S. G. ibid. Chem. Abstr. 1970, 72, 54654.
63. (b) Nebois, P.; Kann, N.; Greene, A. E. J. Org. Chem. 1995, 60, 7690-7692.
64. Vacher, B.; Samat, A.; Allouche, A.; Laknifli, A.; Baldy, A.; Chanon, M. Tetrahedron 1988, 44, 2925-2932.
65. Merbouh, N.; Bobbitt, J. M.; Brückner, C. J. Carbohydr. Chem. 2002, 21, 65-77.
66. Morimoto, H. Yakugaku Zasshi 1955, 75, 916-919;
67. Morimoto, H. ibid. Chem. Abstr. 1956, 50, 24089.
68. Sugawa, T. Yakugaku Zasshi 1957, 77, 332-333;
69. Sugawa, T. ibid. Chem. Abstr. 1957, 51, 62288.
70. Hashimoto, K.; Konno, K.; Shirahama, H. J. Org. Chem. 1996, 61, 4685-4692.
71. Honjo, M. Yakugaku Zasshi 1957, 77, 598-603.
72. Honjo, M. ibid. Chem. Abstr. 1957, 51, 90648.