Synthesis of optically pure 3,4-disubstituted L-glutamates from a novel 2,3-aziridino-γ-lactone 4-carboxylate derivative

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2488-2496

  Dauban, Philippe ^a   Chiaroni, Angèle ^a   Riche, Claude ^a   Dodd, Robert H ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTAMIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0029965369     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951983z     Document Type: Article

References (81)

1. Responsible for the X-ray crystallographic study.
2. For reviews, see: (a) Kalb, R. G. Neuroscientist 1995, 1, 60. (b) Bigge, C. F. Biochem. Pharmacol. 1993, 45, 1547 (c) Nakanishi, S. Science 1992, 258, 597. (d) Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25. (e) Monaghan, D. T.; Bridges, R. J.; Colman, C. W. Annu. Rev. Pharmacol. Toxicol. 1989, 29, 365. (f) Johnson, R. L.; Koerner, J. F. J. Med. Chem. 1988, 31, 2057.
3. For reviews, see: (a) Kalb, R. G. Neuroscientist 1995, 1, 60. (b) Bigge, C. F. Biochem. Pharmacol. 1993, 45, 1547 (c) Nakanishi, S. Science 1992, 258, 597. (d) Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25. (e) Monaghan, D. T.; Bridges, R. J.; Colman, C. W. Annu. Rev. Pharmacol. Toxicol. 1989, 29, 365. (f) Johnson, R. L.; Koerner, J. F. J. Med. Chem. 1988, 31, 2057.
4. For reviews, see: (a) Kalb, R. G. Neuroscientist 1995, 1, 60. (b) Bigge, C. F. Biochem. Pharmacol. 1993, 45, 1547 (c) Nakanishi, S. Science 1992, 258, 597. (d) Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25. (e) Monaghan, D. T.; Bridges, R. J.; Colman, C. W. Annu. Rev. Pharmacol. Toxicol. 1989, 29, 365. (f) Johnson, R. L.; Koerner, J. F. J. Med. Chem. 1988, 31, 2057.
5. For reviews, see: (a) Kalb, R. G. Neuroscientist 1995, 1, 60. (b) Bigge, C. F. Biochem. Pharmacol. 1993, 45, 1547 (c) Nakanishi, S. Science 1992, 258, 597. (d) Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25. (e) Monaghan, D. T.; Bridges, R. J.; Colman, C. W. Annu. Rev. Pharmacol. Toxicol. 1989, 29, 365. (f) Johnson, R. L.; Koerner, J. F. J. Med. Chem. 1988, 31, 2057.
6. For reviews, see: (a) Kalb, R. G. Neuroscientist 1995, 1, 60. (b) Bigge, C. F. Biochem. Pharmacol. 1993, 45, 1547 (c) Nakanishi, S. Science 1992, 258, 597. (d) Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25. (e) Monaghan, D. T.; Bridges, R. J.; Colman, C. W. Annu. Rev. Pharmacol. Toxicol. 1989, 29, 365. (f) Johnson, R. L.; Koerner, J. F. J. Med. Chem. 1988, 31, 2057.
7. For reviews, see: (a) Kalb, R. G. Neuroscientist 1995, 1, 60. (b) Bigge, C. F. Biochem. Pharmacol. 1993, 45, 1547 (c) Nakanishi, S. Science 1992, 258, 597. (d) Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25. (e) Monaghan, D. T.; Bridges, R. J.; Colman, C. W. Annu. Rev. Pharmacol. Toxicol. 1989, 29, 365. (f) Johnson, R. L.; Koerner, J. F. J. Med. Chem. 1988, 31, 2057.
8. Gani, D. Pyridoxal Dependent Systems. In Comprehensive Medicinal Chemistry; Sammes, P. G., Ed.; Pergamon Press: Oxford, 1990; Vol. 2, Chapter 6.5.
9. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
10. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
11. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
12. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
13. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
14. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
15. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
16. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
17. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
18. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
19. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
20. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
21. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
22. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
23. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
24. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
25. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
26. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
27. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
28. Synthesis and biological activities of 3-substituted glutamic acid derivatives: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (b) Yanagida, M.; Hashimoto, K.; Ishida, M., Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. (c) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351. Belokon, Y. N.; Bulychev, A. G., Ryzhov, M. G.; Vitt, S. V.; Batsanov, A.S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865. (e) El Achqar, A.; Boumzebra, M.; Roumestant, M. L., Viallefont, P. Tetrahedron 1988, 44, 5319. (f) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J Org. Chem. 1988, 53, 1947. (g) Kanemasa, S.; Tatsukawa, A.; Wada, E.; Tsuge, O. Chem. Lett. 1989, 1301. (h) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377. (i) Schollkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986 737. (j ) Hartwig, W ; Born, L. J Org. Chem. 1987, 52, 4352. (k) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525. (l) Garner, P. Tetrahedron Lett. 1984, 25, 5855. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866. (n) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Liebigs Ann. Chem. 1994, 641. (o) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021. (p) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org Chem. 1988, 53, 3381. (q) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812. (r) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163. (s) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1989, 54, 498. (t) Suzuki, K.; Seebach, D. Liebigs Ann. Chem 1992, 51
29. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
30. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
31. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
32. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
33. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
34. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
35. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
36. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
37. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
38. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
39. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
40. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
41. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
42. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5,
43. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
44. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
45. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
46. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
47. Synthesis of 4-substituted glutamic acid derivatives: (a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Zee-Cheng, R. K. Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128. Tanaka, K. I.; Yoshifuji, S ; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879. Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283. (e) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453. (f) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859. (g) Del Bosco, M.; Johnstone, A. N. C.; Bazza, G.; Lopatriello, S.; North, M. Tetrahedron 1995, 51, 8545. (h) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401. Hon, Y. S.; Chang, Y. C., Gong, M. L. Heterocycles 1990, 31, 191. (j) Ezquerra, J.; Pedregal, C.; Mico, I.; Najera, C. Tetrahedron: Asymmetry 1994, 5, 921. (k) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409. Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667. (n) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277. (o) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925. (p) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747. (q) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403. (r) Chang, Y. C.; Hon, Y. S.; Chow, W. Y.; Lin, T. A.; Cheng, P. Y.; Wang, C.M. Brain Res. 1993, 604, 86. (s) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518.
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75. As pointed out by a reviewer, the relative proportion of β- to α-anomer decreases in transforming 17 (β:α = 2:1) into the reaction products 21 and 22 (β-21:α-21 + α-22 = 1:1). Because none of the reaction conditions used for this transformation is likely to cause anomerization in favor of the α-anomer, it is more probable that the apparent enrichment in α-anomer may be due to the greater chemical instability of β-21 (or its precursor β-19) compared to α-21 and α-22 under the conditions of the cyclization reaction (DMF and triethylamine at 100°C). Thus, when milder conditions are used (acetonitrile and triethylamine at 82°C), the β:α ratio of the final products remains 2:1, as in the starting material.
76. For a review, see: Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
77. The starting material 19 used for the synthesis of 25 was prepared from 18 using acetonitrile rather than DMF during the cyclization step in order to provide exclusively the β-anomer (together with uncyclized α-20). The small proportion (<10%) of α-25 formed during Cbz-chloride treatment of the mixture of β-19 and 20 is probably the result of the use of DMF and triethylamine in this step, conditions observed to promote cyclization of 20 to α-19.
78. For simplicity of discussion, carbohydrate ring numbering (i.e., as in Scheme 1) has been used throughout for all compounds despite the fact that the ring atoms of some of these compounds (e.g., 24, 27, 29, 32, 34) are numbered differently in the official IUPAC nomenclature (see Experimental Section).
79. The authors have deposited atomic coordinates for compound 24 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK.
80. For a review of the use of carbohydrates for the stereocontrolled synthesis of amino acids, see: Cintas, P Tetrahedron 1991, 47, 6079.
81. We have confirmed that compound 37 reacts with nucleophiles in the same manner as the classical aziridine 2-carboxylic esters. Thus, for example, ethanethiol attacks 37 exclusively at the C-3 position to give the corresponding 3-(ethylthio)-4-hydroxy-L-glutamate derivative. The preparation of a variety of disubstituted glutamates from 37 will be the subject of a separate report.