Investigating carboxylic acid analogues of ambruticin through semi-synthesis

ChemMedChem

Volumn 1, Issue 10, 2006, Pages 1063-1065

  Xu, Yuan ^a   Wang, Zhan ^a   Tian, Zong Qiang ^a   Li, Yong ^a   Shaw, Simon J ^a  

^a KOSAN BIOSCIENCES INC   (United States)

Author keywords

Ambruticin; Analogues; Antifungal agents; Semisynthesis; Structure activity relationships

Indexed keywords

AMBRUTICIN; CARBOXYLIC ACID; PYRAN DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

CARBOXYLIC ACIDS; MOLECULAR CONFORMATION; PYRANS; STEREOISOMERISM;

EID: 33750296074     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200600152     Document Type: Article

References (20)

1. V. T. Andriole, J. Antimicrob. Chemother. 1999, 44, 151-162.
2. a) S. M. Ringel, R. C. Greenough, S. Roemer, D. Connor, A. L. Gutt, B. Blair, G. Kanter, M. von Strandtmann, J. Antibiot. 1977, 30, 371-375;
3. b) G. Höfle, H. Steinmetz, K. Gerth, H. Reichbach, Liebigs Ann. Chem. 1991, 97, 941-945.
4. P. Knauth, H. Reichenbach, J. Antibiot. 2000, 53, 1182-1190.
5. A. S. Kende, Y. Fujii, J. S. Mendoza, J. Am. Chem. Soc. 1990, 112, 9645-9646.
6. a) For a review see V. Michelet, J.-P. Genet, Curr. Org. Chem. 2005, 9, 405-418;
7. b) P. Liu, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 10772-10773;
8. c) T. A. Kirkland, J. Colucci, L. S. Geraci, M. A. Marx, M. Schneider, D. E. Kaelin, Jr, S. F. Martin, J. Am. Chem. Soc. 2001, 123, 12432-12433;
9. d) E. Lee, S. J. Choi, H. Kim, H. O. Han, Y. K. Kim, S. J. Min, S. H. Son, S. M. Lim, W. S. Jang, Angew. Chem. 2002, 114, 184-186;
10. Angew. Chem. Int. Ed. 2002, 47, 176-178.
11. D. T. Connor, M. von Strandtmann, J. Med. Chem. 1979, 22, 1144-1147.
12. D. T. Connor, M. von Strandtmann, J. Med. Chem. 1979, 22, 1055-1059.
13. K. Ishihara, Y. Furuya, H. Yamamoto, Angew. Chem. 2002, 114, 3109-3112;
14. Angew. Chem. Int. Ed. 2002, 47, 2983-2986.
15. S. J. Wittenberger, B. G. Donner, J. Org. Chem. 1993, 58, 4139-4141.
16. a) D. H. R. Barton, D. Crich, W. B. Motherwell, Tetrahedron Lett. 1983, 24, 4979-4982;
17. b) D. H. R. Barton, D. Crich, W. B. Motherwell, Tetrahedron 1985, 47, 3901-3924.
18. T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374.
19. P. Garner, J. T. Anderson, S. Dey, W. J. Youngs, K. Galat, J. Org. Chem. 1998, 63, 5732-5733.
20. NCCLS. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Filamentous Fungi; Approved Standard. Document M38A [ISBN 1-56238-470-8]: National Committee for Clinical Laboratory Standards, Pennsylvania, USA, 2002.