Rigid dipeptide mimetics: Efficient synthesis of enantiopure indolizidinone amino acids

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9437-9446

  Lombart, Henry Georges ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; INDOLIZIDINE DERIVATIVE;

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

EID: 0030446803     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961872f     Document Type: Article

References (66)

1. We have adopted the nomenclature and ring system numbering previously used in refs 3a and 5a in order to maintain clarity and consistency when comparing these different heterocyclic systems.
2. Synthesis and use of 2-oxo-3-phthalimido-7-thia-1-azabicyclo-[4.3.0]nonane-9-carboxylic acid are described in: (a) Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647. (b) Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577.
3. Synthesis and use of 2-oxo-3-phthalimido-7-thia-1-azabicyclo-[4.3.0]nonane-9-carboxylic acid are described in: (a) Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647. (b) Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577.
4. The use of 2-oxo-3-amino-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylic acid in peptide analogues includes: gramicidin S-analogues: (a) Sato, K.; Nagai, U. J. Chem. Soc., Perkin Trans. I 1986, 1231. (b) Bach, A. C., II; Markwalder, J. A.; Ripka, W. C. Int. J. Pept. Protein Res. 1991, 38, 314. Growth hormone-releasing factor analogues: (c) Sato, K.; Hotta, M.; Dong, M.-H.; Hu, H.-Y.; Taulene, J. P.; Goodman, M.; Nagai, U.; Ling, N. Int. J. Pept. Protein Res. 1991, 38, 340. Cyclosporin A analogues: (d) Belshaw, P. J.; Meyer, S. D.; Johnson, D. D.; Romo, D.; Ikeda, Y.; Andrus, M.; Alberg, D. G.; Schultz, L. W.; Clardy, J.; Schreiber, S. L. Synlett 1994, 381. Tendamistat mimetic: (e) Etzkorn, F. A.; Guo, T.; Lipton, M. A.; Goldberg, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1994, 116, 10412. Cyclic RGD peptides: (f) Haubner, R.; Schmitt, W.; Hölzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881. Additional examples, such as enkephalin, LRF, GRF, dermorphin, and somatostatin, are reviewed in ref 2b.
5. The use of 2-oxo-3-amino-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylic acid in peptide analogues includes: gramicidin S-analogues: (a) Sato, K.; Nagai, U. J. Chem. Soc., Perkin Trans. I 1986, 1231. (b) Bach, A. C., II; Markwalder, J. A.; Ripka, W. C. Int. J. Pept. Protein Res. 1991, 38, 314. Growth hormone-releasing factor analogues: (c) Sato, K.; Hotta, M.; Dong, M.-H.; Hu, H.-Y.; Taulene, J. P.; Goodman, M.; Nagai, U.; Ling, N. Int. J. Pept. Protein Res. 1991, 38, 340. Cyclosporin A analogues: (d) Belshaw, P. J.; Meyer, S. D.; Johnson, D. D.; Romo, D.; Ikeda, Y.; Andrus, M.; Alberg, D. G.; Schultz, L. W.; Clardy, J.; Schreiber, S. L. Synlett 1994, 381. Tendamistat mimetic: (e) Etzkorn, F. A.; Guo, T.; Lipton, M. A.; Goldberg, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1994, 116, 10412. Cyclic RGD peptides: (f) Haubner, R.; Schmitt, W.; Hölzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881. Additional examples, such as enkephalin, LRF, GRF, dermorphin, and somatostatin, are reviewed in ref 2b.
6. The use of 2-oxo-3-amino-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylic acid in peptide analogues includes: gramicidin S-analogues: (a) Sato, K.; Nagai, U. J. Chem. Soc., Perkin Trans. I 1986, 1231. (b) Bach, A. C., II; Markwalder, J. A.; Ripka, W. C. Int. J. Pept. Protein Res. 1991, 38, 314. Growth hormone-releasing factor analogues: (c) Sato, K.; Hotta, M.; Dong, M.-H.; Hu, H.-Y.; Taulene, J. P.; Goodman, M.; Nagai, U.; Ling, N. Int. J. Pept. Protein Res. 1991, 38, 340. Cyclosporin A analogues: (d) Belshaw, P. J.; Meyer, S. D.; Johnson, D. D.; Romo, D.; Ikeda, Y.; Andrus, M.; Alberg, D. G.; Schultz, L. W.; Clardy, J.; Schreiber, S. L. Synlett 1994, 381. Tendamistat mimetic: (e) Etzkorn, F. A.; Guo, T.; Lipton, M. A.; Goldberg, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1994, 116, 10412. Cyclic RGD peptides: (f) Haubner, R.; Schmitt, W.; Hölzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881. Additional examples, such as enkephalin, LRF, GRF, dermorphin, and somatostatin, are reviewed in ref 2b.
7. The use of 2-oxo-3-amino-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylic acid in peptide analogues includes: gramicidin S-analogues: (a) Sato, K.; Nagai, U. J. Chem. Soc., Perkin Trans. I 1986, 1231. (b) Bach, A. C., II; Markwalder, J. A.; Ripka, W. C. Int. J. Pept. Protein Res. 1991, 38, 314. Growth hormone-releasing factor analogues: (c) Sato, K.; Hotta, M.; Dong, M.-H.; Hu, H.-Y.; Taulene, J. P.; Goodman, M.; Nagai, U.; Ling, N. Int. J. Pept. Protein Res. 1991, 38, 340. Cyclosporin A analogues: (d) Belshaw, P. J.; Meyer, S. D.; Johnson, D. D.; Romo, D.; Ikeda, Y.; Andrus, M.; Alberg, D. G.; Schultz, L. W.; Clardy, J.; Schreiber, S. L. Synlett 1994, 381. Tendamistat mimetic: (e) Etzkorn, F. A.; Guo, T.; Lipton, M. A.; Goldberg, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1994, 116, 10412. Cyclic RGD peptides: (f) Haubner, R.; Schmitt, W.; Hölzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881. Additional examples, such as enkephalin, LRF, GRF, dermorphin, and somatostatin, are reviewed in ref 2b.
8. The use of 2-oxo-3-amino-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylic acid in peptide analogues includes: gramicidin S-analogues: (a) Sato, K.; Nagai, U. J. Chem. Soc., Perkin Trans. I 1986, 1231. (b) Bach, A. C., II; Markwalder, J. A.; Ripka, W. C. Int. J. Pept. Protein Res. 1991, 38, 314. Growth hormone-releasing factor analogues: (c) Sato, K.; Hotta, M.; Dong, M.-H.; Hu, H.-Y.; Taulene, J. P.; Goodman, M.; Nagai, U.; Ling, N. Int. J. Pept. Protein Res. 1991, 38, 340. Cyclosporin A analogues: (d) Belshaw, P. J.; Meyer, S. D.; Johnson, D. D.; Romo, D.; Ikeda, Y.; Andrus, M.; Alberg, D. G.; Schultz, L. W.; Clardy, J.; Schreiber, S. L. Synlett 1994, 381. Tendamistat mimetic: (e) Etzkorn, F. A.; Guo, T.; Lipton, M. A.; Goldberg, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1994, 116, 10412. Cyclic RGD peptides: (f) Haubner, R.; Schmitt, W.; Hölzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881. Additional examples, such as enkephalin, LRF, GRF, dermorphin, and somatostatin, are reviewed in ref 2b.
9. The use of 2-oxo-3-amino-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylic acid in peptide analogues includes: gramicidin S-analogues: (a) Sato, K.; Nagai, U. J. Chem. Soc., Perkin Trans. I 1986, 1231. (b) Bach, A. C., II; Markwalder, J. A.; Ripka, W. C. Int. J. Pept. Protein Res. 1991, 38, 314. Growth hormone-releasing factor analogues: (c) Sato, K.; Hotta, M.; Dong, M.-H.; Hu, H.-Y.; Taulene, J. P.; Goodman, M.; Nagai, U.; Ling, N. Int. J. Pept. Protein Res. 1991, 38, 340. Cyclosporin A analogues: (d) Belshaw, P. J.; Meyer, S. D.; Johnson, D. D.; Romo, D.; Ikeda, Y.; Andrus, M.; Alberg, D. G.; Schultz, L. W.; Clardy, J.; Schreiber, S. L. Synlett 1994, 381. Tendamistat mimetic: (e) Etzkorn, F. A.; Guo, T.; Lipton, M. A.; Goldberg, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1994, 116, 10412. Cyclic RGD peptides: (f) Haubner, R.; Schmitt, W.; Hölzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881. Additional examples, such as enkephalin, LRF, GRF, dermorphin, and somatostatin, are reviewed in ref 2b.
10. (a) Synthesis of 2-oxo-3-amino-8,8-dimethyl-7-thia-1-azabicyclo-[4.3.0]nonane-9-carboxylic acid is described in: Nagai, U.; Kato, R.; Sato, K.; Ling, N.; Matsuzaki, T.; Tomotake, Y. In Peptides: Chemistry and Biology, Proceedings of the Tenth American Peptide Symposium; Marshall, G. R., Ed.; ESCOM: Leiden, 1988; pp 129-130.
11. (b) Synthesis of 2-oxo-3-amino-8-phenyl-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylic acid is described in: Nagai, U.; Kato, R. Peptides: Chemistry and Structural Biology, Proceedings of the Eleventh American Peptide Symposium; Rivier, J. E.; Marshall, G. R., Eds.; ESCOM: Leiden, 1989; pp 653-654.
12. Syntheses of 2-oxo-5-oxa-3-amino-1-azabicyclo[4.3.0]nonane-9-carboxylic acids are reported in: (a) Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935. (b) Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198.
13. Syntheses of 2-oxo-5-oxa-3-amino-1-azabicyclo[4.3.0]nonane-9-carboxylic acids are reported in: (a) Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935. (b) Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198.
14. Synthesis and analysis of Leu-enkephalin analogues containing 2-oxo-5-oxa-3-amino-1-azabicyclo[4.3.0]nonane-9-carboxylic acid are reported in: Claridge, T. D. W.; Hulme, C.; Kelly, R. J.; Lee, V.; Nash, I. A.; Schofield, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 485.
15. The synthesis of a 2-oxo-3-amino-4-benzyl-1-azabicyclo[4.3.0]-nonane-9-carboxylic acid analogue that serves as a model antagonist of the tachykinin NK-2 receptor is reported in: Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397.
16. The synthesis of 2(S)-amino-3-oxo-11b(R)-hexahydroindolizino-[8,7-b]indole-5(S)-carboxylate is reported in: (a) de la Figuera, N.; Rozas, I.; García-López, M. T.; González-Muñiz, R. J. Chem. Soc., Chem. Commun. 1994, 613. (b) de la Figuera, N.; Alkorta, I.; Rozas, I.; García-López, M. T.; Herranz, R.; González-Muñiz, R. Tetrahedron 1995, 51, 7841.
17. The synthesis of 2(S)-amino-3-oxo-11b(R)-hexahydroindolizino-[8,7-b]indole-5(S)-carboxylate is reported in: (a) de la Figuera, N.; Rozas, I.; García-López, M. T.; González-Muñiz, R. J. Chem. Soc., Chem. Commun. 1994, 613. (b) de la Figuera, N.; Alkorta, I.; Rozas, I.; García-López, M. T.; Herranz, R.; González-Muñiz, R. Tetrahedron 1995, 51, 7841.
18. An alternative strategy to prepare 2-oxo-3-amino-1-azabicyclo-[4.3.0]nonane-9-carboxylic acid is reported in: Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091.
19. The synthesis of a 2-oxo-3-amino-3-benzyl-1-azabicyclo[4.3.0]-nonane-9-carboxylic acid analogue is reported in: Colombo, L.; Di Giacomo, M.; Scolastico, C.; Manzoni, L.; Belvisi, L.; Molteni, V. Tetrahedron Lett. 1995, 36, 625.
20. Preliminary results were reported in part: (a) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147. (b) Lombart, H.-G.; Lubell, W. D. In Peptides 1994 (Proceedings of the 23rd European Peptide Symposium); Maia, H. L. S., Ed.; ESCOM: Leiden 1995; p 696.
21. Preliminary results were reported in part: (a) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147. (b) Lombart, H.-G.; Lubell, W. D. In Peptides 1994 (Proceedings of the 23rd European Peptide Symposium); Maia, H. L. S., Ed.; ESCOM: Leiden 1995; p 696.
22. Lombart, H.-G.; Lubell, W. D. In Peptides: Chemistry, Structure and Biology; Kaumaya, P. T. P, Hodges, R. S., Eds.; ESCOM Sci. Pub. B. V.: Leiden, 1996; p 695.
23. Synthesis of 5-amino-9-oxo-1-azabicyclo[4.3.0]nonane-8-carboxylic acid analogues are described in: Dominguez, M. J.; García-López, M. T.; Herranz, R.; Martin-Martinez, M.; González-Muñiz, R. J. Chem. Soc., Perkin Trans. 1 1995, 2839 and references therein.
24. Synthesis and use of 2-oxo-3-amino-1-azabicyclo[4.3.0]nonane-6-carboxylic acid analogues as type VI β-turn peptide mimetics are described in: (a) Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493. (b) Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861. (c) Kim, K.; Dumas, J.-P.; Germanas, J. P. J. Org. Chem. 1996, 61, 3138. (d) Gramberg, D.; Weber, C.; Beeli, R.; Inglis, J.; Bruns, C.; Robinson, J. A. Helv. Chim. Acta 1995, 78, 1588.
25. Synthesis and use of 2-oxo-3-amino-1-azabicyclo[4.3.0]nonane-6-carboxylic acid analogues as type VI β-turn peptide mimetics are described in: (a) Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493. (b) Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861. (c) Kim, K.; Dumas, J.-P.; Germanas, J. P. J. Org. Chem. 1996, 61, 3138. (d) Gramberg, D.; Weber, C.; Beeli, R.; Inglis, J.; Bruns, C.; Robinson, J. A. Helv. Chim. Acta 1995, 78, 1588.
26. Synthesis and use of 2-oxo-3-amino-1-azabicyclo[4.3.0]nonane-6-carboxylic acid analogues as type VI β-turn peptide mimetics are described in: (a) Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493. (b) Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861. (c) Kim, K.; Dumas, J.-P.; Germanas, J. P. J. Org. Chem. 1996, 61, 3138. (d) Gramberg, D.; Weber, C.; Beeli, R.; Inglis, J.; Bruns, C.; Robinson, J. A. Helv. Chim. Acta 1995, 78, 1588.
27. Synthesis and use of 2-oxo-3-amino-1-azabicyclo[4.3.0]nonane-6-carboxylic acid analogues as type VI β-turn peptide mimetics are described in: (a) Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493. (b) Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861. (c) Kim, K.; Dumas, J.-P.; Germanas, J. P. J. Org. Chem. 1996, 61, 3138. (d) Gramberg, D.; Weber, C.; Beeli, R.; Inglis, J.; Bruns, C.; Robinson, J. A. Helv. Chim. Acta 1995, 78, 1588.
28. 1,4-Diazabicyclo[4.3.0]nonane-9-carboxylic acid analogues are described in: Fobian, Y. M.; d'Avignon, D. A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315.
29. [4.3.0]Pyrazolidinones 2-carboxylic acid analogues have been synthesized as potential antibacterial agents: Ternansky, R. J.; Draheim, S. E. Tetrahedron Lett. 1988, 29, 6569.
30. Recent representative examples of other azabicyclo[X.Y.0]-alkane amino acid derivatives include the following: (a) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914. (b) Flynn, G. A.; Beight, D. W.; Mehdi, S.; Koehl, J. R.; Giroux, E. L.; French, J. F.; Hake, P. W.; Dage, R. C. J. Med. Chem. 1993, 36, 2420. (c) Attwood, M. R.; Hassall, C. H.; Kröhn, A.; Lawton, G.; Redshaw, S. J. Chem. Soc., Perkin Trans. I 1986, 1011. (d) Thomas, W. A.; Whitcombe, I. W. A. J. Chem. Soc., Perkin Trans. II 1986, 747. (e) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (f) Thorsett, E. D. Actual. Chim. Thér. 1886, 13, 257. (g) Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909.
31. Recent representative examples of other azabicyclo[X.Y.0]-alkane amino acid derivatives include the following: (a) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914. (b) Flynn, G. A.; Beight, D. W.; Mehdi, S.; Koehl, J. R.; Giroux, E. L.; French, J. F.; Hake, P. W.; Dage, R. C. J. Med. Chem. 1993, 36, 2420. (c) Attwood, M. R.; Hassall, C. H.; Kröhn, A.; Lawton, G.; Redshaw, S. J. Chem. Soc., Perkin Trans. I 1986, 1011. (d) Thomas, W. A.; Whitcombe, I. W. A. J. Chem. Soc., Perkin Trans. II 1986, 747. (e) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (f) Thorsett, E. D. Actual. Chim. Thér. 1886, 13, 257. (g) Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909.
32. Recent representative examples of other azabicyclo[X.Y.0]-alkane amino acid derivatives include the following: (a) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914. (b) Flynn, G. A.; Beight, D. W.; Mehdi, S.; Koehl, J. R.; Giroux, E. L.; French, J. F.; Hake, P. W.; Dage, R. C. J. Med. Chem. 1993, 36, 2420. (c) Attwood, M. R.; Hassall, C. H.; Kröhn, A.; Lawton, G.; Redshaw, S. J. Chem. Soc., Perkin Trans. I 1986, 1011. (d) Thomas, W. A.; Whitcombe, I. W. A. J. Chem. Soc., Perkin Trans. II 1986, 747. (e) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (f) Thorsett, E. D. Actual. Chim. Thér. 1886, 13, 257. (g) Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909.
33. Recent representative examples of other azabicyclo[X.Y.0]-alkane amino acid derivatives include the following: (a) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914. (b) Flynn, G. A.; Beight, D. W.; Mehdi, S.; Koehl, J. R.; Giroux, E. L.; French, J. F.; Hake, P. W.; Dage, R. C. J. Med. Chem. 1993, 36, 2420. (c) Attwood, M. R.; Hassall, C. H.; Kröhn, A.; Lawton, G.; Redshaw, S. J. Chem. Soc., Perkin Trans. I 1986, 1011. (d) Thomas, W. A.; Whitcombe, I. W. A. J. Chem. Soc., Perkin Trans. II 1986, 747. (e) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (f) Thorsett, E. D. Actual. Chim. Thér. 1886, 13, 257. (g) Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909.
34. Recent representative examples of other azabicyclo[X.Y.0]-alkane amino acid derivatives include the following: (a) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914. (b) Flynn, G. A.; Beight, D. W.; Mehdi, S.; Koehl, J. R.; Giroux, E. L.; French, J. F.; Hake, P. W.; Dage, R. C. J. Med. Chem. 1993, 36, 2420. (c) Attwood, M. R.; Hassall, C. H.; Kröhn, A.; Lawton, G.; Redshaw, S. J. Chem. Soc., Perkin Trans. I 1986, 1011. (d) Thomas, W. A.; Whitcombe, I. W. A. J. Chem. Soc., Perkin Trans. II 1986, 747. (e) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (f) Thorsett, E. D. Actual. Chim. Thér. 1886, 13, 257. (g) Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909.
35. Recent representative examples of other azabicyclo[X.Y.0]-alkane amino acid derivatives include the following: (a) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914. (b) Flynn, G. A.; Beight, D. W.; Mehdi, S.; Koehl, J. R.; Giroux, E. L.; French, J. F.; Hake, P. W.; Dage, R. C. J. Med. Chem. 1993, 36, 2420. (c) Attwood, M. R.; Hassall, C. H.; Kröhn, A.; Lawton, G.; Redshaw, S. J. Chem. Soc., Perkin Trans. I 1986, 1011. (d) Thomas, W. A.; Whitcombe, I. W. A. J. Chem. Soc., Perkin Trans. II 1986, 747. (e) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (f) Thorsett, E. D. Actual. Chim. Thér. 1886, 13, 257. (g) Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909.
36. Recent representative examples of other azabicyclo[X.Y.0]-alkane amino acid derivatives include the following: (a) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914. (b) Flynn, G. A.; Beight, D. W.; Mehdi, S.; Koehl, J. R.; Giroux, E. L.; French, J. F.; Hake, P. W.; Dage, R. C. J. Med. Chem. 1993, 36, 2420. (c) Attwood, M. R.; Hassall, C. H.; Kröhn, A.; Lawton, G.; Redshaw, S. J. Chem. Soc., Perkin Trans. I 1986, 1011. (d) Thomas, W. A.; Whitcombe, I. W. A. J. Chem. Soc., Perkin Trans. II 1986, 747. (e) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (f) Thorsett, E. D. Actual. Chim. Thér. 1886, 13, 257. (g) Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909.
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47. (b) Atfani, M.; Lubell, W. D. J. Org. Chem. 1995, 60, 3184.
48. (c) Zee-Cheng, R. K.-Y.; Olson, R. E. Biochem. Biophys. Res. Commun. 1980, 94, 1128.
49. (a) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1453.
50. (b) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. Tetrahedron 1989, 45, 1465.
51. Bergmeier, S. C.; Cobás, A. A.; Rapoport, H. J. Org. Chem. 1993, 58, 2369.
52. Dimethyl N-(PhF)glutamate was prepared according to the procedure described for dimethyl N-(PhF)aspartate: (a) Jamison, T. F.; Rapoport, H. Org. Synth. 1992, 71, 226. (b) Paz, M. M.; Sardina, J. J. Org. Chem. 1993, 58, 6990. γ-Methyl N-(PhF)glutamate was prepared by esterification according to: (c) Hanby, W. E.; Waley, S. G.; Watson, J. J. Chem. Soc. 1950, 3239. Phenylfluorenation was according to refs 19d and 23a.
53. Dimethyl N-(PhF)glutamate was prepared according to the procedure described for dimethyl N-(PhF)aspartate: (a) Jamison, T. F.; Rapoport, H. Org. Synth. 1992, 71, 226. (b) Paz, M. M.; Sardina, J. J. Org. Chem. 1993, 58, 6990. γ-Methyl N-(PhF)glutamate was prepared by esterification according to: (c) Hanby, W. E.; Waley, S. G.; Watson, J. J. Chem. Soc. 1950, 3239. Phenylfluorenation was according to refs 19d and 23a.
54. Dimethyl N-(PhF)glutamate was prepared according to the procedure described for dimethyl N-(PhF)aspartate: (a) Jamison, T. F.; Rapoport, H. Org. Synth. 1992, 71, 226. (b) Paz, M. M.; Sardina, J. J. Org. Chem. 1993, 58, 6990. γ-Methyl N-(PhF)glutamate was prepared by esterification according to: (c) Hanby, W. E.; Waley, S. G.; Watson, J. J. Chem. Soc. 1950, 3239. Phenylfluorenation was according to refs 19d and 23a.
55. Three different tert-butyl esterification methods were examined in order to synthesize α-tert-butyl γ-methyl N-(PhF)glutamate (2a). γ-Methyl N-(PhF)glutamate was initially prepared by reaction of O-tert-butyl N,N′-diisopropylisourea and γ-methyl N-(PhF)glutamate in 75% yield as described in ref 19d. Comparable yields were obtained, and 2a was conveniently purified when the acid was treated with 400 mol % of N,N-dimethylformamide di-tert-butyl acetal in benzene according to the general procedure described in: (a) Widmer, U. Synthesis 1983, 135. In our hands, the most efficient and least expensive method to prepare 2a employed O-tert-butyl trichloroacetimidate as described in the Experimental Section. This procedure was modified from the methods described in: (b) Armstrong, A.; Brackenridge, I.; Jackson, R. F. W.; Kirk, J. M. Tetrahedron Lett. 1988, 29, 2483. (c) Yue, C.; Thierry, J.; Potier, P. Tetrahedron Lett. 1993, 34, 323. (d) Wessel, H. P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 1985, 2247.
56. Three different tert-butyl esterification methods were examined in order to synthesize α-tert-butyl γ-methyl N-(PhF)glutamate (2a). γ-Methyl N-(PhF)glutamate was initially prepared by reaction of O-tert-butyl N,N′-diisopropylisourea and γ-methyl N-(PhF)glutamate in 75% yield as described in ref 19d. Comparable yields were obtained, and 2a was conveniently purified when the acid was treated with 400 mol % of N,N-dimethylformamide di-tert-butyl acetal in benzene according to the general procedure described in: (a) Widmer, U. Synthesis 1983, 135. In our hands, the most efficient and least expensive method to prepare 2a employed O-tert-butyl trichloroacetimidate as described in the Experimental Section. This procedure was modified from the methods described in: (b) Armstrong, A.; Brackenridge, I.; Jackson, R. F. W.; Kirk, J. M. Tetrahedron Lett. 1988, 29, 2483. (c) Yue, C.; Thierry, J.; Potier, P. Tetrahedron Lett. 1993, 34, 323. (d) Wessel, H. P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 1985, 2247.
57. Three different tert-butyl esterification methods were examined in order to synthesize α-tert-butyl γ-methyl N-(PhF)glutamate (2a). γ-Methyl N-(PhF)glutamate was initially prepared by reaction of O-tert-butyl N,N′-diisopropylisourea and γ-methyl N-(PhF)glutamate in 75% yield as described in ref 19d. Comparable yields were obtained, and 2a was conveniently purified when the acid was treated with 400 mol % of N,N-dimethylformamide di-tert-butyl acetal in benzene according to the general procedure described in: (a) Widmer, U. Synthesis 1983, 135. In our hands, the most efficient and least expensive method to prepare 2a employed O-tert-butyl trichloroacetimidate as described in the Experimental Section. This procedure was modified from the methods described in: (b) Armstrong, A.; Brackenridge, I.; Jackson, R. F. W.; Kirk, J. M. Tetrahedron Lett. 1988, 29, 2483. (c) Yue, C.; Thierry, J.; Potier, P. Tetrahedron Lett. 1993, 34, 323. (d) Wessel, H. P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 1985, 2247.
58. Three different tert-butyl esterification methods were examined in order to synthesize α-tert-butyl γ-methyl N-(PhF)glutamate (2a). γ-Methyl N-(PhF)glutamate was initially prepared by reaction of O-tert-butyl N,N′-diisopropylisourea and γ-methyl N-(PhF)glutamate in 75% yield as described in ref 19d. Comparable yields were obtained, and 2a was conveniently purified when the acid was treated with 400 mol % of N,N-dimethylformamide di-tert-butyl acetal in benzene according to the general procedure described in: (a) Widmer, U. Synthesis 1983, 135. In our hands, the most efficient and least expensive method to prepare 2a employed O-tert-butyl trichloroacetimidate as described in the Experimental Section. This procedure was modified from the methods described in: (b) Armstrong, A.; Brackenridge, I.; Jackson, R. F. W.; Kirk, J. M. Tetrahedron Lett. 1988, 29, 2483. (c) Yue, C.; Thierry, J.; Potier, P. Tetrahedron Lett. 1993, 34, 323. (d) Wessel, H. P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 1985, 2247.
59. Laganis, E. D.; Chenard, B. L. Tetrahedron Lett. 1984, 25, 5831.
60. (a) Krapcho, A. P. Synthesis 1982, 805.
61. (b) Krapcho, A. P. Synthesis 1982, 893.
62. Epimerization of 12 during basic hydrolysis is similar to racemization of N-methylamino esters under similar conditions; see, for examples: Boger, D. L.; Chen, J.-H.; Saionz, K. W. J. Am. Chem. Soc. 1996, 118, 1629 and ref 24 therein.
63. 2 = 0.0828 for all data; GOF = 0.869. The author has deposited the atomic coordinates for the structure of 12 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
64. Ball, J. B.; Alewood, P. F. J. Mol. Recogn. 1990, 3, 55.
65. Madison, V.; Kopple, K. D. J. Am. Chem. Soc. 1980, 102, 4855.
66. We have recently reported a method to prepare L- and D-α-amino dicarboxylates of six to eight carbon chain lengths with high enantiomeric purities: Pham, T.; Lubell, W. D. J. Org. Chem. 1994, 59, 3676.