Total synthesis of chivosazole F

Journal of the American Chemical Society

Volumn 132, Issue 39, 2010, Pages 13610-13611

  Brodmann, Tobias ^a   Janssen, Dominic ^b   Kalesse, Markus ^a,c  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^c HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GENETIC ANALYSIS; MACROLACTONES; STILLE COUPLING; TOTAL SYNTHESIS;

CHIVOSAZOLE F; F ACTIN; MACROLIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIFUNGAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG CYTOTOXICITY; HUMAN; HUMAN CELL; MASS SPECTROMETRY; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STILLE REACTION; SYNTHESIS; WITTIG REACTION;

MACROLIDES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 77957311255     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107290s     Document Type: Article

References (25)

1. Jansen, R., Irschik, H., Reichenbach, H., and Höfle, G. Liebigs Ann. Chem. 1997, 8, 1725-1732
2. Brodmann, T., Lorenz, M., Schäckel, R., Simsek, S., and Kalesse, M. Synlett 2009, 2, 174-192
3. Diestel, R., Irschik, H., Jansen, R., Khalil, M. W., Reichenbach, H., and Sasse, F. ChemBioChem 2009, 10, 2900-2903
4. For cytochalasin D, see
5. Lin, D. C. and Lin, S. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2345-2349
6. Flanagan, M. D. and Lin, S. J. Biol. Chem. 1980, 255, 835-838
7. MacLean-Fletcher, S. and Pollard, T. D. Cell 1980, 20, 329-341 For condramides, see: Kunze, B., Jansen, R., Sasse, F., Höfle, G., and Reichenbach, H. J. Antibiot. 1995, 48, 1262-1266
8. Eggert, U., Diestel, R., Sasse, F., Jansen, R., Kunze, B., and Kalesse, M. Angew. Chem., Int. Ed. 2008, 47, 6478-6482 For rizopodin, see: Sasse, F., Steinmetz, H., Höfle, G., and Reichenbach, H. J. Antibiot. 1993, 46, 741-748
9. Janssen, D., Albert, D., Jansen, R., Müller, R., and Kalesse, M. Angew. Chem., Int. Ed. 2007, 46, 4898-4901
10. Reid, R., Piagentini, M., Rodriguez, E., Ashley, G., Viswanathan, N., Carney, J., Santi, D. V., Hutchinson, C. R., and McDaniel, R. Biochemistry 2003, 42, 72-79
11. Caffrey, P. ChemBioChem 2003, 4, 654-657
12. Paterson, I., Kan, S. B. J., and Gibson, L. J. Org. Lett. 2010, 12, 3724-3727
13. Brodmann, T., Janssen, D., Sasse, F., Irschik, H., Jansen, R., Müller, R., and Kalesse, M. Eur. J. Org. Chem. 2010, 5155 - 5159
14. Janssen, D. and Kalesse, M. Synlett 2007, 17, 2667-2670
15. Ghosh, A. K., Wang, Y., and Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982
16. Mapp, A. K. and Heathcock, C. H. J. Org. Chem. 1999, 64, 23-27
17. Marshall, J. A., Eidam, P., and Schenk Eidam, H. J. Org. Chem. 2006, 71, 4840-4844
18. Marshall, J. A. Chem. Rev. 2000, 100, 3163-3186
19. Williams, D. R., Brooks, D. A., and Berliner, M. A. J. Am. Chem. Soc. 1999, 121, 4924-4925
20. Phillips, A. J., Uto, Y., Wipf, P., Reno, M. J., and Williams, D. R. Org. Lett. 2000, 2, 1165-1168
21. Tamura, R., Kato, M., Saegusa, K., Kakihana, M., and Oda, D. J. Org. Chem. 1987, 52, 4121-4124
22. Tamura, R., Saegusa, K., Kakihana, M., and Oda, D. J. Org. Chem. 1988, 53, 2723-2728
23. Milstein, D. and Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636-3638 For reviews, see: Duncton, M. A. J. and Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1999, 1235-1246
24. Pattenden, G. and Sinclair, D. J. J. Organomet. Chem. 2002, 653, 261-268
25. Nicolaou, K. C., Bulger, P. G., and Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489