Stereocontrolled construction of substituted pyrrolidines based on intramolecular protodesilylation reaction. Enantiospecific synthesis of (-)-kainic acid and (+)-allokainic acid from L-serine

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 2, 1993, Pages 125-127

  Hatakeyama, Susumi ^a   Sugawara, Kazutoshi ^a   Takano, Seiichi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049082226     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39930000125     Document Type: Article

References (23)

1. S. Hatakeyama, K. Sugawara, M. Kawamura and S. Takano, Tetrahedron Lett., 32, 4509.
2. S. Hatakeyama, K. Sugawara and S. Takano, Tetrahedron Lett., 32, 4513.
3. S. Hatakeyama, K. Sugawara and S. Takano, J. Chem. Soc., Chem. Commun., 1533.
4. S. Hatakeyama, K. Sugawara and S. Takano, J. Chem. Soc., Chem. Commun., 953.
5. C. Georgoulis, W. Smadja and J.M. Valery, Synthesis, 572, For the related reactions of 1-alkyl- and 1,1-dialkyl-allenes with iodine, see.
6. R.W. Friesen and A.E. Kolaczewska, J. Org. Chem., 56, 4888, references cited therein.
7. K. Hashimoto and H. Shirahama, J. Synth. Org. Chem. Jpn., 47, 212, For reviews on the synthesis of the kainoids, see.
8. R.M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford.
9. Kainic Acids as a Tool in Neurobiology, E. G. McGeer, J. W. Olney, P. L. McGeer, Raven Press, New York.
10. O. Goldberg, A. Luini and V.I. Teichberg, J. Med. Chem., 26, 39.
11. S.R. Wilson and M.F. Price, J. Am. Chem. Soc., 104, 1124, For intramolecular protodesilylation of allyl silanes, see.
12. S.R. Wilson and M.F. Price, Tetrahedron Lett., 24, 569.
13. S. Takano, T. Sugihara, S. Satoh and K. Ogasawara, J. Am. Chem. Soc., 110, 6467, For the synthesis of kainic acid, see: ref. 3 and.
14. S. Takano, Y. Iwabuchi and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1204.
15. S. Takano, K. Inomata and K. Ogasawara, J. Chem. Soc., Chem. Commun., 169.
16. J. Cooper, D.W. Knight and P.T. Gallagher, J. Chem. Soc., Perkin Trans. 1, 553, references cited therein.
17. W. Oppolzer, C. Robbiani and K. Büttig, Tetrahedron, 40, 1341, For the synthesis of allokainic acid, see: ref. 3 and.
18. A. Barco, S. Benetti, A. Casolari, G.P. Pollini and G. Spalluto, Tetrahedron Lett., 31, 4917.
19. H.H. Mooiweer, H. Hiemstra and W.N. Speckamp, Tetrahedron, 47, 3451, references cited therein.
20. W.C. Still and C. Gennari, Tetrahedron Lett., 24, 4405.
21. B. Giese, Radicals in Organic Synthesis: Formation of Carbon–Carbon Bonds, 5, For reviews on radical cyclisations, see: J. E. Baldwin, Pergamon, New York.
22. C. Thebtaranonth and Y. Thebtaranonth, Tetrahedron, 46, 1385.
23. M. Ihara, K. Yasui, N. Taniguchi and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1469, Cf.