Enterobactin and enantioenterobactin

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3548-3550

  Marinez, Eric R ^a   Salmassian, Eric K ^a   Lau, Thomas T ^a   Gutierrez, Carlos G ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENTEROCHELIN;

ARTICLE; DRUG SYNTHESIS;

EID: 0029942855     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9520194     Document Type: Article

References (28)

1. Pollack, J. R.; Nielands, J. B. Biochem. Biophys. Res. Commun. 1970, 38, 989. O'Brien, I. G.; Gibson, F. Biochem. Biophys. Acta 1970, 215, 393.
2. Pollack, J. R.; Nielands, J. B. Biochem. Biophys. Res. Commun. 1970, 38, 989. O'Brien, I. G.; Gibson, F. Biochem. Biophys. Acta 1970, 215, 393.
3. Rutz, J. M.; Abdullah, T.; Singh, S. P.; Kalve, V. I.; Klebba, P. E. J Bacteriol. 1991, 173, 5964
4. Loomis, L. D.; Raymond, K. N. Inorg. Chem. 1991, 30, 906.
5. Rastetter, W. H.; Erickson, T. J.; Venuti, M. C. J. Org Chem. 1980, 45, 5012. Rastetter, W. H.; Erickson, T. J.; Venuti, M. C. J. Org. Chem. 1981, 46, 3579.
6. Rastetter, W. H.; Erickson, T. J.; Venuti, M. C. J. Org Chem. 1980, 45, 5012. Rastetter, W. H.; Erickson, T. J.; Venuti, M. C. J. Org. Chem. 1981, 46, 3579.
7. Karpishin, T. B.; Dewey, T. M.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 1842. Karpishin, T. B.; Raymond, K. N. Angew. Chem. 1992, 104, 486
8. Karpishin, T. B.; Dewey, T. M.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 1842. Karpishin, T. B.; Raymond, K. N. Angew. Chem. 1992, 104, 486
9. Raymond, K. N. Pure Appl Chem. 1994, 66, 773 and references therein.
10. (a) Shanzer, A.; Libman, J. J. Chem. Soc., Chem. Commun. 1983, 846.
11. (b) Shanzer, A.; Libman, J.; Lifson, S., Felder, C. E. J. Am. Chem. Soc. 1986, 108, 7609
12. Guttman, St.; Boissonnas, R. A. Helv. Chim. Acta 1958, 41, 1852. Guttman, St. Helv. Chim. Acta 1962, 45, 2622.
13. Guttman, St.; Boissonnas, R. A. Helv. Chim. Acta 1958, 41, 1852. Guttman, St. Helv. Chim. Acta 1962, 45, 2622.
14. A superior preparation of N-tritylamino acids is presented by: Barlos, K.; Papaioannou, D.; Theodoropolous, D. J. Org. Chem. 1982, 47, 1324.
15. Shanzer, A.; Libman, J.; Frolow, F. J. Am. Chem. Soc. 1981, 103, 7339.
16. Corey, E. J.; Bhattaracharyya, S. Tetrahedron Lett. 1977, 3919.
17. (a) Arnold, L. D.; Kalantar, T. H., Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105.
18. (b) Arnold, L. D.; Drover, J. C. G; Vederas, J. C. J. Am. Chem. Soc. 1987, 109, 4649.
19. (c) Arnold, L. D., May, R. G.; Vederas, J. C. J. Am. Chem Soc. 1988, 110, 2237.
20. (d) Pansare, S. V.; Arnold, L. D.; Vederas, J. C. Org. Synth. 1991, 70, 10
21. (e) Ramer, S. E.; Moore, R. N.; Vederas, J. C. Can. J. Chem. Soc. 1986, 64, 706.
22. Roelens, S. J. Chem. Soc., Chem. Commun. 1990, 58.
23. Plattner, D. A.; Brunner, A.; Dobler, M.; Müller, H.-M.; Petter, W.; Zbinden, P.; Seebach, D. Helv. Chim. Acta 1993, 76, 2004.
24. The more readily commercially available diethyl azodicarboxylate (DEAD) can be used in place of DMAD, although chromatograpic separation of the product is generally easier with the latter.
25. Considine, W. J. J. Organomet. Chem. 1966, 5, 263.
26. Schuda, P. F.; Botti, C. M.; Venuti, M. O.P.P.I. Briefs 1984, 16, 119-25.
27. Anhydrous ethanoLic HCl is conveniently prepared by adding freshly distilled acetyl chloride (1.6 mL, 22.5 mmol) to 25 mL of anhydrous ethanol, followed by titration with a standard NaOH solution, using 0.25% phenolphthalein in ethanol as indicator.
28. RSB-35 is a surface active agent marketed by Pierce Chemical Co.