An enantioselective synthesis of differentially protected erythro-α,β-diamino acids and its application to the synthesis of an analogue of rhodopeptin B5

Journal of Organic Chemistry

Volumn 68, Issue 1, 2003, Pages 35-42

  Durham, Timothy B ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC PEPTIDES;

ESTERS; SYNTHESIS (CHEMICAL);

ORGANIC ACIDS;

ALPHA AMINO ACID; ANTIFUNGAL AGENT; BETA AMINO ACID; BETA LACTAM DERIVATIVE; CYCLOLYSYLVALYL(2 AMINO 3 DECYL BETA ALANYL)GLYCINE; DIAMINO ACID; ESTER DERIVATIVE; FUNCTIONAL GROUP; RHODOPEPTIN B5; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CANDIDA PARAPSILOSIS; CRYPTOCOCCUS NEOFORMANS; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; REACTION ANALYSIS; STEREOSPECIFICITY;

AMINO ACIDS; ANTIFUNGAL AGENTS; BETA-LACTAMS; COMBINATORIAL CHEMISTRY TECHNIQUES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; STEREOISOMERISM;

EID: 0037427991     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo016276m     Document Type: Article

References (39)

1. Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: New York, 1989.
2. Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650.
3. Andruskiewicz, R. Pol. J. Chem. 1998, 72, 1-48.
4. Calmes, M.; Daunis, J. Amino Acids 1999, 16, 215-250.
5. Yet, L. Angew. Chem., Int. Ed. 2001, 40, 875-877.
6. Miller, M. J. J. Org. Chem. 1980, 45, 3131-3132.
7. Hoffman, C.; Tanke, R. S.; Miller, M. J. J. Org. Chem. 1989, 54, 3750-3751.
8. Dolence, E. K.; Minnick, A. A.; Miller, M. J. J. Med. Chem. 1990, 33, 461-464.
9. Roosenberg, I. J. M.; Lin, Y.-M.; Lu, Y.; Miller, M. J. Curr. Med. Chem. 2000, 7, 159-197.
10. Shireman, B. T.; Miller, M. J. J. Org. Chem. 2001, 66, 4809-4813.
11. Ojima, I. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; pp 197-255.
12. Ojima, I. Advances in Asymmetric Synthesis; JAI Press Inc.: Stamford, CT, 1995; Vol. 1, pp 95-146.
13. Ojima, I.; Pei, Y. Tetrahedron Lett. 1990, 31, 977-980.
14. Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. Chem. Commun. 1996, 633-634.
15. Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. K. J. J. Am. Chem. Soc. 1980, 102, 7026-7032.
16. Gasparski, C. M.; Teng, M.; Miller, M. J. J. Am. Chem. Soc. 1992, 114, 2741-2743.
17. Teng, M.; Miller, M. J. J. Am. Chem. Soc. 1993, 115, 548-554.
18. Bellettini, J. R.; Miller, M. J. J. Org. Chem. 1996, 61, 7959-7962.
19. For a discussion of an alternative mechanistic rationale for this transformation see: Hoffman, R. V. In The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science; Greenberg, A., Breneman, C. M., Liebman, J. F., Eds.; John Wiley & Sons: New York, 2000; pp 137-155.
20. Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1992; pp 295-368.
21. Guzzo, P. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4862-4867.
22. Durham, T. B.; Miller, M. J. J. Org. Chem., in press.
23. Ojima, I.; Sun, C. M.; Zucco, M.; Park, Y. H.; Duclos, O.; Kuduk, S. Tetrahedron Lett. 1993, 34, 4149-4152.
24. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498.
25. Palomo, C.; Aizpurua, J. M.; Cuevas, C. J. Chem. Soc., Chem. Commun. 1994, 1957-1958.
26. Palomo, C.; Aizpurua, J. M.; Cuevas, C.; Mieglo, A.; Galarza, R. Tetrahedron Lett. 1995, 36, 9027-9030.
27. Brooks, D. W.; de Lee, N. C.; Peevey, R. Tetrahedron Lett. 1984, 25, 4623-4626.
28. Pirrung, M. C.; Chau, J. H.-L. J. Org. Chem. 1995, 60, 8084-8085.
29. Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424-2426.
30. Chiba, H.; Agematu, H.; Kaneto, R.; Terasawa, T.; Sakai, K.; Dobashi, K.; Yoshioka, T. J. Antibiot. 1999, 52, 695-699.
31. Nakayama, K.; Kawato, H. C.; Inagaki, H.; Nakajima, R.; Kitamura, A.; Someya, K.; Ohta, T. Org. Lett. 2000, 2, 977-980.
32. Kawato, H. C.; Nakayama, K.; Inagaki, H.; Ohta, T. Org. Lett. 2001, 3, 3451-3454.
33. Nakayama, K.; Kawato, H. C.; Inagaki, H.; Ohta, T. Org. Lett. 2001, 3, 3447-3450.
34. Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227-4230.
35. Chiba, H.; Agematu, H.; Sakai, K.; Dobashi, K.; Yoshioka, T. J. Antibiot. 1999, 52, 710-720.
36. Kawato, H. C.; Nakayama, K.; Inagaki, H.; Nakajima, R.; Kitamura, A.; Someya, K.; Ohta, T. Org. Lett. 2000, 2, 973-976.
37. Regitz, M.; Hocker, J.; Liedhegener, A. In Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, pp 179-184.
38. Hutchinson, C. R.; Nakane, M.; Gollman, H.; Knutson, P. L. In Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, pp 323-325.
39. Fino, J. R.; Mattingly, P. G.; Ray, K. A. Bioconjugate Chem.1996, 7, 274-280.