Synthesis of α-kainic acid from a 7-azabicyclo[2.2.1]heptadiene by tandem radical addition-homoallylic radical rearrangement

Organic Letters

Volumn 7, Issue 5, 2005, Pages 815-817

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

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; IODINE DERIVATIVE; KAINIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE;

ADDITION REACTION; ARTICLE; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

ALKENES; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; INDICATORS AND REAGENTS; KAINIC ACID; MOLECULAR STRUCTURE;

EID: 15044353670     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047557u     Document Type: Article

References (29)

1. (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic: 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. Moloney, M. G. Nat. Prod. Rep. 1998, 15, 205-219.
7. Goldberg, O.; Luini, A.; Teichberg, V. I. Tetrahedron Lett. 1980, 21, 2355-2358.
8. Leung-Toung, R.; Liu, Y.; Muchowski, J. M.; Wu, Y.-L. J. Org. Chem. 1998, 63, 3235-3250.
9. Malpass, J. R.; White, R. J. Org. Chem. 2004, 69, 5328-5334. See also: 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.
10. Malpass, J. R.; White, R. J. Org. Chem. 2004, 69, 5328-5334. See also: 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.
11. 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.
12. Arakawa, Y.; Yasuda, M.; Ohnishi, M.; Yoshifuji, S. Chem. Pharm. Bull. 1997, 45, 255-259.
13. (a) For a review of α-kainic acid syntheses, see: Parsons, A. F. Tetrahedron 1996, 52, 4149-4174.
14. For selected recent syntheses, see: (b) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139-11143. (c) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 3194-3204. (d) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485-487. (e) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727-4733. (f) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467-1470. (g) Martinez, M. M.; Hoppe, D. Org. Lett. 2004, 6, 3743-3746.
15. For selected recent syntheses, see: (b) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139-11143. (c) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 3194-3204. (d) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485-487. (e) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727-4733. (f) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467-1470. (g) Martinez, M. M.; Hoppe, D. Org. Lett. 2004, 6, 3743-3746.
16. For selected recent syntheses, see: (b) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139-11143. (c) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 3194-3204. (d) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485-487. (e) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727-4733. (f) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467-1470. (g) Martinez, M. M.; Hoppe, D. Org. Lett. 2004, 6, 3743-3746.
17. For selected recent syntheses, see: (b) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139-11143. (c) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 3194-3204. (d) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485-487. (e) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727-4733. (f) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467-1470. (g) Martinez, M. M.; Hoppe, D. Org. Lett. 2004, 6, 3743-3746.
18. For selected recent syntheses, see: (b) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139-11143. (c) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 3194-3204. (d) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485-487. (e) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727-4733. (f) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467-1470. (g) Martinez, M. M.; Hoppe, D. Org. Lett. 2004, 6, 3743-3746.
19. For selected recent syntheses, see: (b) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139-11143. (c) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 3194-3204. (d) Xia, Q.; Ganem, B. Org. Lett. 2001, 3, 485-487. (e) Clayden, J.; Menet, C. J.; Tchabanenko, K. Tetrahedron 2002, 58, 4727-4733. (f) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467-1470. (g) Martinez, M. M.; Hoppe, D. Org. Lett. 2004, 6, 3743-3746.
20. Aldehydic compounds 10-14 were unstable to chromatography and were used without further purification to prepare carbonate 15.
21. Baldwin, J. E.; Turner, S. C. M.; Moloney, M. G. Synlett 1994, 925-928.
22. Krafft, M. E.; Cheung, Y. Y.; Abboud, K. A. J. Org. Chem. 2001, 66, 7443-7448.
23. (a) Baldwin, J. E.; Fryer, A. M.; Pritchard, G. J. J. Org. Chem. 2001, 66, 2588-2596.
24. (b) Ahern, D. G.; Seguin, R. J.; Filer, C. N. J. Labelled Compd. Radiopharm. 2002, 45, 401-405.
25. Goldberg, O.; Luini, A.; Teichberg, V. I. J. Med. Chem. 1983, 26, 39-42.
26. Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S.; Tomasini, C. J. Org. Chem. 1984, 49, 701-703.
27. Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
28. 1H NMR spectrum.
29. Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179-11193.