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Volumn 40, Issue 20, 1999, Pages 3873-3876

From phenylaziridine to phenylkainoids. A formal synthesis of (±)- phenylkainic acid

Author keywords

Allylsilane; Aziridine; Phenylkainoid; Pyrrolidine

Indexed keywords

KAINIC ACID DERIVATIVE; PHENYLKAINIC ACID; UNCLASSIFIED DRUG;

EID: 0033553380     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00611-5     Document Type: Article
Times cited : (19)

References (26)
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    • 5. For a recent review on kainoid amino acid chemistry see: Parsons, A. F. Tetrahedron 1966, 52, 4149-4174. For recent syntheses of kainic acid see: Cossy, J.; Cases, M.; Pardo, D. G. Synlett 1998, 507-509. Rubio, A.; Ezquerra, J.; Escribano, A; Remuinan, M. J.; Vaquerro, J. J. Tetrahedron Lett. 1998, 39, 2171-2174. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun. 1999, 245-246.
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    • 5. For a recent review on kainoid amino acid chemistry see: Parsons, A. F. Tetrahedron 1966, 52, 4149-4174. For recent syntheses of kainic acid see: Cossy, J.; Cases, M.; Pardo, D. G. Synlett 1998, 507-509. Rubio, A.; Ezquerra, J.; Escribano, A; Remuinan, M. J.; Vaquerro, J. J. Tetrahedron Lett. 1998, 39, 2171-2174. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun. 1999, 245-246.
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    • 5. For a recent review on kainoid amino acid chemistry see: Parsons, A. F. Tetrahedron 1966, 52, 4149-4174. For recent syntheses of kainic acid see: Cossy, J.; Cases, M.; Pardo, D. G. Synlett 1998, 507-509. Rubio, A.; Ezquerra, J.; Escribano, A; Remuinan, M. J.; Vaquerro, J. J. Tetrahedron Lett. 1998, 39, 2171-2174. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun. 1999, 245-246.
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    • 6. For syntheses of phenylkainic acid see: Horikawa, M.; Shirahama, H. Synlett 1996, 95-96. Hashimoto, K; Horikawa, M.; Shirahama, H. Tetrahedron Lett. 1990, 31, 7047-7051. Baldwin, J. E.; Rudolph, M. Tetrahedron lett. 1994, 33, 6163-6166. Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Withehead, R. C; Wood, M. E. Tetrahedron Lett 1996, 37, 6923-26. Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658-2659. Maeda, H.. Kraus, G. A. J. Org. Chem. 1997, 62, 2314-2315. Maeda, H.; Selvakumar, N.; Kraus, G. A. Tetrahedron 1999, 55, 943-954.
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    • 6. For syntheses of phenylkainic acid see: Horikawa, M.; Shirahama, H. Synlett 1996, 95-96. Hashimoto, K; Horikawa, M.; Shirahama, H. Tetrahedron Lett. 1990, 31, 7047-7051. Baldwin, J. E.; Rudolph, M. Tetrahedron lett. 1994, 33, 6163-6166. Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Withehead, R. C; Wood, M. E. Tetrahedron Lett 1996, 37, 6923-26. Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658-2659. Maeda, H.. Kraus, G. A. J. Org. Chem. 1997, 62, 2314-2315. Maeda, H.; Selvakumar, N.; Kraus, G. A. Tetrahedron 1999, 55, 943-954.
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    • 6. For syntheses of phenylkainic acid see: Horikawa, M.; Shirahama, H. Synlett 1996, 95-96. Hashimoto, K; Horikawa, M.; Shirahama, H. Tetrahedron Lett. 1990, 31, 7047-7051. Baldwin, J. E.; Rudolph, M. Tetrahedron lett. 1994, 33, 6163-6166. Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Withehead, R. C; Wood, M. E. Tetrahedron Lett 1996, 37, 6923-26. Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658-2659. Maeda, H.. Kraus, G. A. J. Org. Chem. 1997, 62, 2314-2315. Maeda, H.; Selvakumar, N.; Kraus, G. A. Tetrahedron 1999, 55, 943-954.
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    • 6. For syntheses of phenylkainic acid see: Horikawa, M.; Shirahama, H. Synlett 1996, 95-96. Hashimoto, K; Horikawa, M.; Shirahama, H. Tetrahedron Lett. 1990, 31, 7047-7051. Baldwin, J. E.; Rudolph, M. Tetrahedron lett. 1994, 33, 6163-6166. Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Withehead, R. C; Wood, M. E. Tetrahedron Lett 1996, 37, 6923-26. Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658-2659. Maeda, H.. Kraus, G. A. J. Org. Chem. 1997, 62, 2314-2315. Maeda, H.; Selvakumar, N.; Kraus, G. A. Tetrahedron 1999, 55, 943-954.
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    • note
    • 2S: C, 70.76; H, 6.41; N, 4.15. Found C, 70.88; H, 6.55; N, 4.25
  • 24
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