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Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4304-4314

Stereocontrolled synthesis of 5α- and 5β-substituted kainic acids

(5) Collado, Iván a Ezquerra, Jesus a Mateo, Ana I a Pedregal, Concepción a Rubio, Almudena a

a ELI LILLY AND COMPANY (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

KAINIC ACID;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033546265 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo982109j Document Type: Article

Times cited : (20)

References (77)

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11
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- For some leading references to synthesis of kainic acid, see: (a) Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978. (b) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1987, 166. (c) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1204. (d) Takano, S. Sugihara, T., Sotoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467. (e) Cooper, J.; Knight, S. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. (f) Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G. P.; Zanirato, V. J. Org. Chem. 1992, 57, 6279. (g) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. (h) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (i) Yoo, S-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968. (j) Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773. (k) Bachi, M. D.; Melman, A. Synlett 1996, 60. (l) Bachi, M. D.; Bar-Ner, N.; Melman, A. J. Org. Chem. 1996, 61, 7116. (m) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (n) Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857. (o) Rubio, A.; Ezquerra, J.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron Lett. 1998, 39, 2171. For rewiews, see: Synthesis of Optically Active α-Amino Acids: Williams, R. M., Ed.; Pergamon Press: New York, 1989; p 305. Parsons, A. F. Tetrahedron 1996, 52, 4149.
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12
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- For some leading references to synthesis of kainic acid, see: (a) Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978. (b) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1987, 166. (c) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1204. (d) Takano, S. Sugihara, T., Sotoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467. (e) Cooper, J.; Knight, S. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. (f) Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G. P.; Zanirato, V. J. Org. Chem. 1992, 57, 6279. (g) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. (h) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (i) Yoo, S-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968. (j) Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773. (k) Bachi, M. D.; Melman, A. Synlett 1996, 60. (l) Bachi, M. D.; Bar-Ner, N.; Melman, A. J. Org. Chem. 1996, 61, 7116. (m) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (n) Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857. (o) Rubio, A.; Ezquerra, J.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron Lett. 1998, 39, 2171. For rewiews, see: Synthesis of Optically Active α-Amino Acids: Williams, R. M., Ed.; Pergamon Press: New York, 1989; p 305. Parsons, A. F. Tetrahedron 1996, 52, 4149.
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- For some leading references to synthesis of kainic acid, see: (a) Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978. (b) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1987, 166. (c) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1204. (d) Takano, S. Sugihara, T., Sotoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467. (e) Cooper, J.; Knight, S. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. (f) Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G. P.; Zanirato, V. J. Org. Chem. 1992, 57, 6279. (g) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. (h) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (i) Yoo, S-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968. (j) Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773. (k) Bachi, M. D.; Melman, A. Synlett 1996, 60. (l) Bachi, M. D.; Bar-Ner, N.; Melman, A. J. Org. Chem. 1996, 61, 7116. (m) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (n) Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857. (o) Rubio, A.; Ezquerra, J.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron Lett. 1998, 39, 2171. For rewiews, see: Synthesis of Optically Active α-Amino Acids: Williams, R. M., Ed.; Pergamon Press: New York, 1989; p 305. Parsons, A. F. Tetrahedron 1996, 52, 4149.
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14
- 37049072532
- For some leading references to synthesis of kainic acid, see: (a) Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978. (b) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1987, 166. (c) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1204. (d) Takano, S. Sugihara, T., Sotoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467. (e) Cooper, J.; Knight, S. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. (f) Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G. P.; Zanirato, V. J. Org. Chem. 1992, 57, 6279. (g) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. (h) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (i) Yoo, S-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968. (j) Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773. (k) Bachi, M. D.; Melman, A. Synlett 1996, 60. (l) Bachi, M. D.; Bar-Ner, N.; Melman, A. J. Org. Chem. 1996, 61, 7116. (m) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (n) Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857. (o) Rubio, A.; Ezquerra, J.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron Lett. 1998, 39, 2171. For rewiews, see: Synthesis of Optically Active α-Amino Acids: Williams, R. M., Ed.; Pergamon Press: New York, 1989; p 305. Parsons, A. F. Tetrahedron 1996, 52, 4149.
- (1992) J. Chem. Soc., Chem. Commun. , pp. 169
- Takano, S.¹ Inomata, K.² Ogasawara, K.³

15
- 37049082226
- For some leading references to synthesis of kainic acid, see: (a) Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978. (b) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1987, 166. (c) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1204. (d) Takano, S. Sugihara, T., Sotoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467. (e) Cooper, J.; Knight, S. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. (f) Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G. P.; Zanirato, V. J. Org. Chem. 1992, 57, 6279. (g) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. (h) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (i) Yoo, S-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968. (j) Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773. (k) Bachi, M. D.; Melman, A. Synlett 1996, 60. (l) Bachi, M. D.; Bar-Ner, N.; Melman, A. J. Org. Chem. 1996, 61, 7116. (m) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (n) Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857. (o) Rubio, A.; Ezquerra, J.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron Lett. 1998, 39, 2171. For rewiews, see: Synthesis of Optically Active α-Amino Acids: Williams, R. M., Ed.; Pergamon Press: New York, 1989; p 305. Parsons, A. F. Tetrahedron 1996, 52, 4149.
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- Hatakeyama, S.¹ Sugawara, K.² Takano, S.³

16
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- For some leading references to synthesis of kainic acid, see: (a) Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978. (b) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1987, 166. (c) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1204. (d) Takano, S. Sugihara, T., Sotoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467. (e) Cooper, J.; Knight, S. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. (f) Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G. P.; Zanirato, V. J. Org. Chem. 1992, 57, 6279. (g) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. (h) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (i) Yoo, S-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968. (j) Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773. (k) Bachi, M. D.; Melman, A. Synlett 1996, 60. (l) Bachi, M. D.; Bar-Ner, N.; Melman, A. J. Org. Chem. 1996, 61, 7116. (m) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (n) Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857. (o) Rubio, A.; Ezquerra, J.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron Lett. 1998, 39, 2171. For rewiews, see: Synthesis of Optically Active α-Amino Acids: Williams, R. M., Ed.; Pergamon Press: New York, 1989; p 305. Parsons, A. F. Tetrahedron 1996, 52, 4149.
- (1994) J. Org. Chem. , vol.59 , pp. 6968
- Yoo, S.-E.¹ Lee, S.H.²

17
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- For some leading references to synthesis of kainic acid, see: (a) Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978. (b) Baldwin, J. E.; Li, C.-S. J. Chem. Soc., Chem. Commun. 1987, 166. (c) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1204. (d) Takano, S. Sugihara, T., Sotoh, S.; Ogasawara, K. J. Am. Chem. Soc. 1988, 110, 6467. (e) Cooper, J.; Knight, S. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. (f) Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G. P.; Zanirato, V. J. Org. Chem. 1992, 57, 6279. (g) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. (h) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (i) Yoo, S-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968. (j) Monn, J. A.; Valli, M. J. J. Org. Chem. 1994, 59, 2773. (k) Bachi, M. D.; Melman, A. Synlett 1996, 60. (l) Bachi, M. D.; Bar-Ner, N.; Melman, A. J. Org. Chem. 1996, 61, 7116. (m) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (n) Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857. (o) Rubio, A.; Ezquerra, J.; Remuiñán, M. J.; Vaquero, J. J. Tetrahedron Lett. 1998, 39, 2171. For rewiews, see: Synthesis of Optically Active α-Amino Acids: Williams, R. M., Ed.; Pergamon Press: New York, 1989; p 305. Parsons, A. F. Tetrahedron 1996, 52, 4149.
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18
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- The NOEs observed in 21 and 4 are shown below: equation presented
- The NOEs observed in 21 and 4 are shown below: equation presented

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.