Synthesis of streptolydigin, a potent bacterial RNA polymerase inhibitor

Journal of the American Chemical Society

Volumn 132, Issue 41, 2010, Pages 14394-14396

  Pronin, Sergey V ^a   Kozmin, Sergey A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASSEMBLY PROCESS; BROAD SPECTRUM ANTIBIOTICS; DESILYLATION; DIECKMANN CYCLIZATION; LINEAR SEQUENCE; NATURAL PRODUCTS; ONE-POT PROCEDURES; RNA POLYMERASE; STREPTOMYCES LYDICUS; WADSWORTH-EMMONS OLEFINATION;

BACTERIOLOGY;

RNA;

ENZYME INHIBITOR; RNA POLYMERASE; STREPTOLYDIGIN;

ACYLATION; ARTICLE; DESILYLATION; DIECKMANN REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HORNER WADSWORTH EMMONS REACTION; SILYLATION; STEREOCHEMISTRY;

AMINOGLYCOSIDES; DNA-DIRECTED RNA POLYMERASES; STREPTOMYCES;

EID: 77958075743     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107190w     Document Type: Article

References (41)

1. DeBoer, C., Dietz, A., Silver, W. S., and Savage, G. M. Antibiotics Ann. 1956, 886-892
2. Eble, T. E., Large, C. M., DeVries, W. H., Crum, G. F., and Shell, J. W. Antibiotics Ann. 1956, 893-896
3. Lewis, C., Wilkins, J. R., Schwartz, D. F., and Nikitas, C. T. Antibiotics Ann. 1956, 897-902
4. Siddhikol, C., Erbstoeszer, J. W., and Weiblum, B. J. Bacteriol. 1969, 99, 151-155
5. Temiakov, D., Zenkin, N., Vassylyeva, M. N., Perederina, A., Tahirov, T. H., Kashkina, E., Savkina, M., Zorov, S., Nikiforov, V., Igarashi, N., Matsugaki, N., Wakatsuki, S., Severinov, K., and Vassylyev, D. G. Mol. Cell 2005, 19, 655-666
6. Tuske, S. Cell 2005, 122, 541-552
7. Vassylyev, D. G., Vassylyeva, M. N., Zhang, J., Palangat, M., Artsimovitch, I., and Landick, R. Nature 2007, 448, 163-169
8. Miropolskaya, N., Artsimovitch, I., Klimasauskas, S., Nikiforov, V., and Kulbachinskiy, A. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 18942-18947
9. Fisher, L. Bull. Natl. Tuberc. Respir. Dis. Assoc. 1971, 57, 11-12
10. Xu, M., Zhou, Y. N., Goldstein, B. P., and Jin, D. J. J. Bacteriol. 2005, 187, 2783-2792
11. Rinehart, K. L., Jr., Beck, J. R., Epstein, W. W., and Spicer, L. D. J. Am. Chem. Soc. 1963, 85, 4035-4037
12. Rinehart, K. L., Jr. and Borders, D. B. J. Am. Chem. Soc. 1963, 85, 4037-4038
13. Rinehart, K. L., Jr., Beck, J. R., Borders, D. B., Kinstle, T. H., and Krauss, D. J. Am. Chem. Soc. 1963, 85, 4038-4039
14. Duchamp, D. J., Branfman, A. R., Button, A. C., and Rinehart, K. L., Jr. J. Am. Chem. Soc. 1973, 95, 4077-4078
15. Brill, G. M., McAlpine, J. B., and Whittern, D. J. Antibiot. 1988, 41, 36-44
16. Meyer, C. F. J. Antibiot. 1971, 24, 558-560
17. Karwowski, J. P., Jackson, M., Theriault, R. J., Barlow, G. J., Coen, L., Hensey, D. M., and Humphey, P. E. J. Antibiot. 1992, 45, 1125-1132
18. Schlessinger, R. H., Bebernitz, G. R., Lin, P., and Poss, A. J. J. Am. Chem. Soc. 1985, 107, 1777-1778
19. DeShong, P., Ramesh, S., Elango, V., and Perez, J. J. Am. Chem. Soc. 1985, 107, 5219-5224
20. Boeckman, R. K., Starrett, J. E., Nickell, D. G., and Sum, P. E. J. Am. Chem. Soc. 1986, 108, 5549-5559
21. Neukom, C., Richardson, D. P., Myerson, J. H., and Bartlett, P. A. J. Am. Chem. Soc. 1986, 108, 5559-5568
22. Shimshock, S. J., Waltermire, R. E., and DeShong, P. J. Am. Chem. Soc. 1991, 113, 8791-8796
23. Iwata, Y., Maekawara, N., Tanino, K., and Miyashita, M. Angew. Chem., Int. Ed. 2005, 44, 1532-1536
24. Boeckman, R. K., Jr., Potenza, J. C., and Enholm, E. J. J. Org. Chem. 1987, 52, 469-472
25. Schlessinger, R. H. and Graves, D. D. Tetrahedron Lett. 1987, 28, 4385-4388
26. Ireland, R. E. and Smith, M. G. J. Am. Chem. Soc. 1988, 110, 854-860
27. Ley, S. V. and Woodward, P. R. Tetrahedron Lett. 1987, 28, 345-346
28. Ley, S. V., Smith, S. C., and Woodward, P. R. Tetrahedron 1992, 48, 1145-1174
29. Cartwright, D., Lee, V. J., and Rinehart, K. L. J. Am. Chem. Soc. 1978, 100, 4237-4239
30. Kolb, H. C., VanNieuwenhze, M. S., and Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547
31. Ester 12 was prepared in three steps from benzyl acrylate as described in the Supporting Information.
32. Solsona, J. G., Nebot, J., Romea, P., and Urpi, F. J. Org. Chem. 2005, 70, 6533-6536
33. Evans, D. A. and Hoveyda, A. J. Am. Chem. Soc. 1990, 112, 6447-6449
34. Garber, S. V., Kingsbury, J. S., Gray, B. L., and Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179
35. Preparation of known acid 20 is described in the Supporting Information.
36. Evans, D. A. and Britton, T. C. J. Am. Chem. Soc. 1987, 109, 6881-6883
37. Rhodinose 7 was prepared in five steps from alcohol 11 as described in the Supporting Information.
38. 13C NMR analysis, see
39. Lee, V. J. and Rinehart, K. L. J. Antibiot. 1980, 33, 408-415
40. DiCioccio, R. A., Srivastana, B. I. S., Rinehart, K. L., Lee, V. J., Branfman, A. R., and Li, L.-H. Biochem. Pharmacol. 1980, 29, 2001-2008
41. Olano, C., Gómez, C., Pérez, M., Palomino, M., Pineda-Lucena, A., Carbajo, R. J., Braña, A. F., Méndez, C., and Salas, J. A. Chem. Biol. 2009, 16, 1031-1044