Total synthesis and assignment of the side chain stereochemistry of LI-F04a: An antimicrobial cyclic depsipeptide

Organic Letters

Volumn 12, Issue 15, 2010, Pages 3394-3397

  Cochrane, James R ^a   McErlean, Christopher S P ^a   Jolliffe, Katrina A ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; DEPSIPEPTIDE; LI F04A PEPTIDE, BACILLUS; LI-F04A PEPTIDE, BACILLUS;

ARTICLE; BACILLUS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTI-INFECTIVE AGENTS; ANTIFUNGAL AGENTS; BACILLUS; BACTERIAL PROTEINS; DEPSIPEPTIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77955149886     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101254m     Document Type: Article

References (31)

1. Brickner, S. J.; Mobashery, S. Curr. Opin. Microbiol. 2007, 10, 425
2. Lipsitch, M. Trends Microbiol. 2004, 8, 515
3. Barrett, J. F. Expert Opin. Ther. Targets 2005, 9, 253
4. Lamagni, T. L.; Evans, B. G.; Shigematsu, M.; Johnson, E. M. Epidemiol. Infect. 2001, 126, 397
5. Pfaller, M. A. Clin. Infect. Dis. 1998, 27, 1148-1150.13
6. Marr, K. A.; Carter, R. A.; Crippa, F.; Wald, A.; Corey, L. Clin. Infect. Dis. 2002, 34, 909
7. Norby, S. R.; Nord, C. E.; Finch, R. Lancet Infect. Dis. 2005, 5, 115
8. Kaneda, M.; Kajimura, Y. Yakugaku Zasshi 2002, 122, 651
9. Kuroda, J.; Fukai, T.; Konishi, M.; Uno, J.; Kurusu, K.; Nomura, T. Heterocycles 2000, 53, 1533
10. Choi, S. K.; Park, S. Y.; Kim, R.; Lee, C. H.; Kim, J. F.; Park, S. H. Biochem. Biophys. Res. Commun. 2008, 365, 89
11. Kajimura, Y.; Kaneda, M. J. Antibiot. 1996, 49, 129
12. Kajimura, Y.; Kaneda, M. J. Antibiot. 1997, 50, 220
13. Kajimura, Y.; Sugiyama, M.; Kaneda, M. J. Antibiot. 1995, 48, 1095
14. Kurusu, K.; Ohba, K.; Arai, T.; Fukushima, K. J. Antibiot. 1987, 40, 1506
15. Stawikowski, M.; Cudic, P. Tetrahedron Lett. 2006, 47, 8587
16. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391
17. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307
18. Liang, Q.; Sun, Y.; Yu, B.; She, X.; Pan, X. J. Org. Chem. 2007, 72, 9846
19. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989
20. Sarabia, F.; Chammaa, S.; Lopez-Herrera, F. J. Tetrahedron Lett. 2002, 43, 2961
21. Carpita, A.; Mannocci, L.; Rossi, R. Eur. J. Org. Chem. 2005, 1859
22. Dodd, D. S.; Kozikowski, A. P. Tetrahedron Lett. 1994, 35, 977
23. Djerassi, C.; Engle, R. R. J. Am. Chem. Soc. 1953, 75, 3838
24. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936
25. Joo, J. E.; Pham, V. T.; Tian, Y. S.; Chung, Y. S.; Oh, C. Y.; Lee, K. Y.; Ham, W. H. Org. Biomol. Chem. 2008, 6, 1498
26. Bollhagen, R.; Schiedberger, M.; Barlos, K.; Grell, E. J. Chem. Soc., Chem. Commun. 1994, 2559
27. Kopple, K. D. J. Pharm. Sci. 1972, 61, 1345
28. Ehrlich, A.; Heyne, H.-U.; Winter, R.; Beyermann, M.; Haber, H.; Carpino, L. A.; Bienert, M. J. Org. Chem. 1996, 61, 8831
29. Hikota, M.; Sakurai, Y.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1990, 31, 6367
30. Isidro-Llobet, A.; Álvarez, M.; Albericio, F. Chem. Rev. 2009, 109, 2455
31. He, H. Y.; Shen, B.; Korshalla, J.; Carter, G. T. Tetrahedron 2001, 57, 1189