Stereoselective synthesis of optically active β-lactams, potential inhibitors of pilus assembly in pathogenic bacteria

Organic Letters

Volumn 2, Issue 14, 2000, Pages 2065-2067

  Emtenäs, Hans ^a   Soto, Gabe ^b   Hultgren, Scott J ^b   Marshall, Garland R ^c   Almqvist, Fredrik ^a  

^a UMEÅ UNIVERSITY   (Sweden)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BETA LACTAM;

ARTICLE; BACTERIUM; CONFORMATION; DRUG EFFECT; FIMBRIA; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTI-BACTERIAL AGENTS; BACTERIA; BETA-LACTAMS; CRYSTALLOGRAPHY, X-RAY; FIMBRIAE, BACTERIAL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0034643990     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0059899     Document Type: Article

References (26)

1. For a review on the use of penicillin: see Nathwani, D.; Wood, M. J. Drugs 1993, 45, 866. For other representative examples, see: (a) Chemistry and Biology of β-lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3.
2. For a review on the use of penicillin: see Nathwani, D.; Wood, M. J. Drugs 1993, 45, 866. For other representative examples, see: (a) Chemistry and Biology of β-lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3.
3. (b) Brown, A. G. Pure Appl. Chem. 1987, 59, 475.
4. (a) The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie Academic and Professional: New York, 1996.
5. (b) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
6. Ojima, I.; Lin, S. J. Org. Chem. 1998, 63, 224-225.
7. (a) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333-2342.
8. (b) Stephens, C.; Shapiro, L. Chem. Biol. 1997, 4, 637-641.
9. Hultgren, S. J.; Abraham, S.; Caparon, M.; Falk, P.; St. Gerne, J. W., III; Normark, S. Cell 1993, 73, 887-901.
10. Hemmer Karlsson, K.; Waise, B.; Drakenberg, T.; Roy, S.; Bergquist, K.-E.; Pinkner, J. S.; Hultgren, S. J.; Kihlberg, J. Bioorg. Med. Chem. 1998, 6, 2085-2101.
11. (a) Kuehn, M. J.; Ogg, D. J.; Kihlberg, J.; Slonim, L. N.; Flemmer, K.; Bergfors. T.; Hultgren, S. J. Science 1993, 262, 1234-1241.
12. (b) Soto, G. E.; Dodson, K. W.; Ogg, D.; Liu, C.; Heuser, J.; Knight, S.; Kihlberg, J.; Jones, C. H.; Hultgren, S. J. EMBO J. 1998, 17, 6155-6167.
13. (a) Sauer, F. G.; Fütterer, K.; Pinkner, J. S.; Dodson, K. W.; Hultgren, S. J.; Waksman, G. Science 1999, 285, 1058-1061.
14. (b) Choudhury, D.; Thompson, A.; Stojanoff, V.; Langermann, S.; Pinkner, J.; Hultgren, S. J.; Knight, S. D. Science 1999, 285, 1062-1066.
15. Plattner, J. J.; Norbeck, D. W. Obstacles to drug development from peptide leads; Clark, C. R., Moos, W. R., Eds.; Ellis Harwood Ltd.-Halstead Press: Chichester, England, 1989; pp 92-126.
16. (a) Higaki, J. N.; Chakravarty, S.; Bryant, C. M.; Cowart, L. R.; Harden, P.; Scardina, J. M.; Mavunkel, B.; Luedtke, G. R.; Cordell, B. J. Med. Chem. 1999, 42, 3889-3898.
17. (b) Siev, D. V.; Semple, J. E. Org. Lett. 2000, 2, 19-22.
18. (a) Staudinger, H. Liebigs Ann. Chem. 1907, 356, 51-123.
19. (b) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; Chapter 6.
20. Bose, A. K.; Manhas, M. S.; Chib, J. S.; Chawla, H. P. S.; Dayal, B. J. Org. Chem. 1974, 39, 2877-2884.
21. Nagao, Y.; Kumagai, T.; Abe, S. T. T.; Ochiai, M.; Inoue, Y.; Taga, T.; Fujita, E. J. Org. Chem. 1986, 51, 4739-4741.
22. (a) Yamamoto, Y.; Watanabe, Y.; Ohnishi, S. Chem. Pharm. Bull. 1987, 35, 1860-1870.
23. (b) Yamamoto, Y.; Watanabe, Y. Chem. Pharm. Bull. 1987, 35, 1871-1879.
24. 4S 342.0800; observed 342.0803.
25. Almqvist, F.; Guillaume, D.; Hultgren S. J.; Marshall, G. R. Tetrahedron Lett. 1998, 39, 2293-2294.
26. 2-thiazoline 2 was re-formed during the reaction, suggesting that a retro opening of the β-lactam ring, catalyzed by the electrophilic reducing agent, was a competing side reaction.