Enantiospecific synthesis of 3,4-disubstituted glutamic acids via controlled stepwise ring-opening of 2,3-aziridino-γ-lactone

Tetrahedron Letters

Volumn 43, Issue 42, 2002, Pages 7593-7595

  Yan, Zhaohua ^a   Weaving, Robert ^a   Dauban, Philippe ^a   Dodd, Robert H ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; GLUTAMIC ACID DERIVATIVE; LACTONE DERIVATIVE; RIBOSE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; DEPROTECTION REACTION; ENANTIOMER; HYDROGENOLYSIS; REGULATORY MECHANISM; TRANSESTERIFICATION;

EID: 0037078437     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01762-8     Document Type: Article

References (31)

1. For recent and relevant reviews on excitatory amino acids pharmacology, see: (a) Bräuner-Osborne, H.; Egebjerg, J.; Nielsen, E. Ø.; Madsen, U.; Krogsgaard-Larsen, P. J. Med. Chem. 2000, 43, 2609-2645; (b) Moloney, M. G. Nat. Prod. Rep. 1999, 16, 485-498; © Doble, A. Pharmacol. Ther. 1999, 81, 163-221.
2. For recent and relevant reviews on excitatory amino acids pharmacology, see: (a) Bräuner-Osborne, H.; Egebjerg, J.; Nielsen, E. Ø.; Madsen, U.; Krogsgaard-Larsen, P. J. Med. Chem. 2000, 43, 2609-2645; (b) Moloney, M. G. Nat. Prod. Rep. 1999, 16, 485-498; © Doble, A. Pharmacol. Ther. 1999, 81, 163-221.
3. For recent and relevant reviews on excitatory amino acids pharmacology, see: (a) Bräuner-Osborne, H.; Egebjerg, J.; Nielsen, E. Ø.; Madsen, U.; Krogsgaard-Larsen, P. J. Med. Chem. 2000, 43, 2609-2645; (b) Moloney, M. G. Nat. Prod. Rep. 1999, 16, 485-498; © Doble, A. Pharmacol. Ther. 1999, 81, 163-221.
4. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
5. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
6. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
7. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
8. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
9. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
10. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
11. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
12. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
13. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
14. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
15. For recent examples, see: (a) Bunch, L.; Johansen, T. H.; Bräuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Bioorg. Med. Chem. 2001, 9, 875-879; (b) Pedregal, C.; Collado, I.; Escribano, A.; Ezquerra, J.; Dominguez, C.; Mateo, A. I.; Rubio, A.; Baker, S. R.; Goldsworthy, J.; Kamboj, R. K.; Ballyk, B. A.; Hoo, K.; Bleakman, D. J. Med. Chem. 2000, 43, 1958-1968; © Baker, S. R.; Bleakman, D.; Ezquerra, J.; Ballyk, B. A.; Deverill, M.; Ho, K.; Kamboj, R. K.; Collado, I.; Dominguez, C.; Escribano, A.; Mateo, A. I.; Pedregal, C.; Rubio, A. Bioorg. Med. Chem. Lett. 2000, 10, 1807-1810; (d) Ma, D.; Tang, G.; Tian, H.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Guillena, G.; Mancheño, B.; Nájera, C.; Ezquerra, J.; Pedregal, C. Tetrahedron 1998, 54, 9447-9456; (f) Escribano, A.; Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Baker, S. R.; Wright, R. A.; Johnson, B. G.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1998, 8, 765-770; (g) Receveur, J.-M.; Guiramand, J.; Récasens, M.; Roumestant, M.-L.; Viallefont, P.; Martinez, J. Bioorg. Med. Chem. Lett. 1998, 8, 127-132; (h) Helaine, V.; Bolte, J. Tetrahedron: Asymmetry 1998, 9, 3855-3861; (i) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170; (j) Wermuth, C. G.; Mann, A.; Schoenfelder, A.; Wright, R. A.; Johnson, B. G.; Burnett, J. P.; Mayne, N. G.; Schoepp, D. D. J. Med. Chem. 1996, 39, 814-816; (k) Gu, Z. Q.; Hesson, D. P.; Pelletier, J. C.; Maccechini, M. L.; Zhou, L. M.; Skolnick, P. J. Med. Chem. 1995, 38, 2518-2520; (l) For a review of previous syntheses of substituted glutamic acids, see: Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488-2496.
16. Oba M., Koguchi S., Nishiyama K. Tetrahedron Lett. 42:2001;5901-5902.
17. Langlois N. Tetrahedron Lett. 40:1999;8801-8803.
18. Dubois L., Dodd R.H. Tetrahedron. 49:1993;901-910.
19. Dubois L., Mehta A., Tourette E., Dodd R.H. J. Org. Chem. 59:1994;434-441.
20. Dauban P., Dubois L., Tran Huu Dau E., Dodd R.H. J. Org. Chem. 60:1995;2035-2043.
21. Dauban P., Dodd R.H. J. Org. Chem. 62:1997;4277-4284.
22. Dauban P., Hofmann B., Dodd R.H. Tetrahedron. 53:1997;10743-10752.
23. De Saint-Fuscien C., Tarrade A., Dauban P., Dodd R.H. Tetrahedron Lett. 41:2000;6393-6397.
24. Dauban P., De Saint-Fuscien C., Dodd R.H. Tetrahedron. 55:1999;7589-7600.
25. Dauban P., De Saint-Fuscien C., Acher F., Prézeau L., Brabet I., Pin J.-P., Dodd R.H. Bioorg. Med. Chem. Lett. 10:2000;129-133.
26. Seebach D., Hungerbühler E., Naef R., Schnurrenberger P., Weidmann B., Züger M. Synthesis. 1982;138-141.
27. Shapiro G., Marzi M. J. Org. Chem. 62:1997;7096-7097.
28. The epimerization at the C-4 position could be related to the Lewis acidity of the titanium complexes.
29. It should be mentioned that such a controlled lactone ring-opening reaction was also performed with 2,3-aziridino-γ-lactone 6 in the presence of benzyl alcohol, but in rather poor yield (<35%).
30. 4 in toluene in the presence of 5 equiv. of benzyl alcohol.
31. 3OD) δ 53.4, 58.0, 79.2, 82.9, 173.0, 178.2.