An Enantioselective Synthesis of (-)-α-Kainic Acid via Thiyl Radical Addition-Cyclization-Elimination Reaction

Synlett

Volumn 1997, Issue 3, 1997, Pages 275-276

  Miyata, Okiko ^a   Ozawa, Yoshiki ^a   Ninomiya, Ichiya ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001688764     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-784     Document Type: Article

References (16)

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2. Review: Parsons, A. F. Tetrahedron 1996, 52, 4145.
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4. We have reported the thiyl radical addition-cyclization for the heterocycle synthesis. a) Naito, T.; Honda, U.; Miyata, O.; Ninomiya, I. J. Chem. Soc. Perkin Trans. 1 1995, 19. b) Miyata, O.; Nishiguchi, A.; Ninomiya, I.; Naito, T. Tetrahedron Lett. 1996, 37, 229.
5. We have reported the thiyl radical addition-cyclization for the heterocycle synthesis. a) Naito, T.; Honda, U.; Miyata, O.; Ninomiya, I. J. Chem. Soc. Perkin Trans. 1 1995, 19. b) Miyata, O.; Nishiguchi, A.; Ninomiya, I.; Naito, T. Tetrahedron Lett. 1996, 37, 229.
6. Bertrand and co-workers have reported an attempted synthesis of kainic acid via the tosyl radical mediated cyclization in which tosyl radical is generated from unstable and commercially unavailable Se-phenyl tolueneselenosulfonate (PhSeTs). : Bertrand, M.-P.; Gastaldi, S; Nouguier, R. Tetrahedron Lett. 1996, 37, 1229.
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12. 3).
13. 1H-NMR spectrum with those of the isomer 5 and the related compounds prepared and unpublished.
14. 13 upon comparison of their spectral data.
15. Yoo, S.; Lee, S. H. J. Org. Chem. 1994, 59, 6968.
16. Takano, S.; Sugihara, T.; Satoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467.