Novel approach to the (-)-sparteine-mediated synthesis of kainoids: Total synthesis of (-)-α-kainic acid by (-)-sparteine-mediated deprotonation

European Journal of Organic Chemistry

Volumn , Issue 7, 2005, Pages 1427-1443

  Martínez, M Montserrat ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

( ) Sparteine; Allyl carbamates; Asymmetric synthesis; Natural products; Pyrrolidines

Indexed keywords

ALLYL COMPOUND; CARBAMIC ACID; GLUTAMIC ACID; KAINIC ACID; LITHIUM; PROTON; PYRROLIDINE DERIVATIVE; SERINE; SPARTEINE;

ALKYLATION; ARTICLE; CHIRALITY; CYCLIZATION; MOLECULAR INTERACTION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 16444381572     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400824     Document Type: Article

References (53)

1. For a preliminary communication of our work see: M. M. Martínez, D. Hoppe, Org. Lett. 2004, 6, 3743-3746.
2. a) L. Rodney, J. Johnson, F. Koerner, J. Med. Chem. 1988, 31, 2057-2062 and references cited therein;
3. b) J. C. Watkins, P. Krogsgaard-Larsen, P. Honoré, Trends Pharmacol. Sci. 1990, 11, 25-33;
4. c) J. C. Watkins, in: Kainic Acid as a Tool in Neurobiology (Eds.: E. G. McGeer, J. W. Olney, P. L. McGeer), Raven Press, New York, 1978, pp. 26-69.
5. K. Hashimoto, Y. Ohfune, H. Shirahama, Tetrahedron Lett. 1995, 36, 6235-6238.
6. J. C. Watkins, R. H. Evans, Annu. Pharmacol. Toxicol. 1981, 21, 165-166.
7. W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979.
8. a) For review see: A. F. Parsons, Tetrahedron 1996, 52, 4149-4174.
9. 〈lit6b〉For review see: R. M. Williams in: Synthesis of Optically Active a-Amino Acids, Pergamon Press, Oxford, 1989, pp. 306-320;
10. c) For selected syntheses of (-)-α-kainic acid see: K. Hashimoto, H. Shirahama, J. Synth. Org. Chem. Jpn. 1989, 47, 212-223;
11. d) H. Nakagawa, T. Sugahara, K. Ogasawara, Org. Lett. 2000, 2, 3181-3183;
12. e) Q. Xia, B. Ganem. Org. Lett. 2001, 3, 485-487;
13. f) J. Clayden, C. J. Menet, K. Tchabanenko, Tetrahedron 2002, 55, 4727-4733;
14. g) O. Miyata, Y. Ozawa, I. Ninomiya, T. Naito, Tetrahedron 2000, 56, 6199-6207;
15. h) B. M. Trost, M. T. Rudd, Org. Lett. 2003, 5, 1467-1470;
16. i) M. V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139-11143;
17. j) A. D. Campbell, T. M. Raynham, R. J. K. Taylor, J. Chem. Soc. Perkin Trans. 1 2000, 19, 3194-3204;
18. k) H. Hirasawa, T. Taniguchi, K. Ogasawara, Tetrahedron Lett. 2001, 42, 7587-7590;
19. l) S. E. Yoo, S. H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435-3438;
20. m) S. Takano, T. Sugihara, S. Satoh, K. Ogasawara, J. Am. Chem. Soc. 1988, 110, 6467-6471.
21. A. Deiters, D. Hoppe, J. Org. Chem. 2001, 66, 2842-2849.
22. A. Deiters, B. Wibbeling, D. Hoppe, Adv. Synth. Catal. 2001, 1, 181-183.
23. K. Shimamoto, M. Ishida, H. Shinozaki, Y. Ohfune, J. Org. Chem. 1991, 56, 4167-4176.
24. See experimental section for more details.
25. J. Tsuji, I. Minami, I. Shimizu, H. Kataoka, Chem. Lett. 1984, 1133-1136.
26. a) F. Hintze, D. Hoppe, Synthesis 1992, 1216-1218;
27. b) P. Michan, A. Rassat, Bull. Soc. Chim. Fr. 1971, 3561-3562;
28. c) D. Hoppe, F. Hintze, P. Tebben, Angew. Chem. Int. Ed. Engl. 1990, 29, 1422-1423.
29. E. Corey, A. Venkateswarlu, J. Am. Chem. Soc. 1972, 94, 6190-6192.
30. K. M. Bertini Gross, P. Beak, J. Am. Chem. Soc. 2001, 123, 315-321.
31. N-Benzylation was carried out by reductive amination, see: A. Barco, S. Benetti, G. Spalluto, J. Org. Chem. 1992, 57, 6279-6286.
32. 4) unsuccessfully.
33. C. Prakash, S. Saleh, I. A. Blair. Tetrahedron Lett. 1989, 30, 19-22.
34. a) K. Kondo, Y. Kondo, T. Takemoto, T. IKenoue, Bull. Chem. Soc. Jpn. 1962, 35, 1899-1900;
35. b) For a discusion the rotameric distribution of several kainoids, see: G. A. Conway, J. S. Park, L. Maggiora, M. P. Merles, N. Galton, E. K. Michaelis, J. Med. Chem. 1984, 27, 52-56;
36. c) A. P. Kozikowski, A. H. Fauq, Tetrahedron Lett. 1990, 31, 2967-2970, and references therein.
37. a) P. Kocienski, N. J. Dixon, Synlett 1989, 52-54;
38. b) P. Kocienski, C. Barber, Pure Appl. Chem. 1990, 62, 1933-1940.
39. S. Hanessian, S. Ninkovic, J. Org. Chem. 1996, 61, 5418-5424.
40. Synthesized from α-hydroxyacetone in 67% overall yield over four steps: silylation followed by Horner-Wadsworth-Emmons reaction, 1,2-reduction of ester moiety and bromination.
41. A. Deiters, C. Mück-Lichtenfeld, R. Fröhlich, D. Hoppe, Org. Lett. 2000, 2, 2415-2418.
42. H. Günther in: NMR-Spektroskopie, Georg Thieme Verlag, Stuttgart, New York, 1992. The coupling constants were obtained with the use of packet of programs TURBOMOLE (vers 5.6), University of Karlsruhe, 2003. The structures were obtimized with the theoretical function at the DFT level using the pure B-P functional [DFT(B-P)] and the basis set TZVP (triplevalence-polarized).
43. a) In all known examples, deprotonation of O-allylic carbamates with n-BuLi/(-)-sparteine led to the (5)-configured organo-lithium compound. For review see: D. Hoppe, T. Hense, Angw. Chem. Int. Ed. Engl. 1997, 36, 2282-2316, and references therein;
44. b) D. Hoppe, F. Marr, M. Bruggemann in: Organolithiums in Enantioselective Synthesis in Topics in Organometallic Chemistry (Ed.: D. M. Hodgson), Springer-Verlag, Berlin, Heidelberg, 2003, vol. 5, pp. 61-67.
45. a) D. Hoppe, A. Brönneke, Tetrahedron Lett. 1983, 24, 1687-1693;
46. N-reactions, see: M. R. Magid, Tetrahedron 1980, vol. 5, 1901-1930.
47. a) F. Rehders, D. Hoppe, Synthesis 1992, 859-864;
48. b) A. P. Grieco, T. Oguri, Y. Yokoyama, Tetrahedron Lett. 1978, 19, 419-420.
49. D. Madec, V. Henryon, P. J. Férézou, Tetrahedron Lett. 1999, 40, 8103-8107.
50. M. Seppi, R. Kalkofen, J. Reupohl, R. Fröhlich, D. Hoppe, Angew. Chem. Int. Ed. 2004, 43, 1423-1427.
51. H. Paulsen, D. Hoppe, Tetrahedron 1992, 48, 5667-5670.
52. A. D. Campbell, T. M. Raynham, R. J. K. Taylor, Chem. Commun. 1999, 245-246.
53. [6i,6j]). The NOE studies were carried out at low temperature because of the broad signals.