Enantioselective synthesis of pactamycin, a complex antitumor antibiotic

Science

Volumn 340, Issue 6129, 2013, Pages 180-182

  Malinowski, Justin T ^a   Sharpe, Robert J ^a   Johnson, Jeffrey S ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE; PACTAMYCIN; RNA 16S;

ANTIBIOTICS; CYTOLOGY; MAMMAL; PHYLOGENETICS; THREE-DIMENSIONAL MODELING; TUMOR;

ARTICLE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; GENETIC ENGINEERING; MANNICH REACTION; PHYLOGENY; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

EID: 84876337427     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1234756     Document Type: Article

References (32)

1. Y.-W. Chin, M. J. Balunas, H. B. Chai, A. D. Kinghorn, AAPS J. 8, E239 (2006).
2. F. von Nussbaum, M. Brands, B. Hinzen, S. Weigand, D. Habich, Angew. Chem. Int. Ed. 45, 5072 (2006).
3. C. Drahl, B. F. Cravatt, E. J. Sorensen, Angew. Chem. Int. Ed. 44, 5788 (2005).
4. K. Nakanishi, in Comprehensive Natural Products Chemistry, D. Barton et al ., Eds. (Elsevier, New York, 1999), vol. 1, p. 23.
5. A. D. Argoudelis, H. K. Jahnke, J. A. Fox, Antimicrob. Agents Chemother. 1962, 191 (1962).
6. G. Dinos et al., Mol. Cell 13, 113 (2004).
7. D. D. Weller, A. Haber, K. L. Rinehart Jr., P. F. Wiley, J. Antibiot. 31, 997 (1978).
8. P. F. Wiley, H. K. Jahnke, F. MacKellar, R. B. Kelly, A. D. Argoudelis, J. Org. Chem. 35, 1420 (1970).
9. D. J. Duchamp, abstract no. 23 presented at the American Crystallographic Association Winter Meeting, Albuquerque, NM, 3 to 7 April 1972.
10. D. E. Brodersen et al., Cell 103, 1143 (2000).
11. M. Iwatsuki et al., J. Antibiot. 65, 169 (2012).
12. W. Lu, N. Roongsawang, T. Mahmud, Chem. Biol. 18, 425 (2011).
13. K. Otoguro et al., J. Antibiot. 63, 381 (2010).
14. K. Dobashi et al., J. Antibiot. 39, 1779 (1986).
15. For an instructive debate on this point, please see (16).
16. J. D. Keasling, A. Mendoza, P. S. Baran, Nature 492, 188 (2012).
17. S. Hanessian et al., Angew. Chem. Int. Ed. 50, 3497 (2011).
18. S. Hanessian, R. R. Vakiti, S. Dorich, S. Banerjee, B. Deschênes-Simard, J. Org. Chem. 77, 9458 (2012).
19. T. Tsujimoto, T. Nishikawa, D. Urabe, M. Isobe, Synlett 2005, 433 (2005).
20. S. Knapp, Y. Yu, Org. Lett. 9, 1359 (2007).
21. J. T. Malinowski, S. J. McCarver, J. S. Johnson, Org. Lett. 14, 2878 (2012).
22. T. J. Haussener, R. E. Looper, Org. Lett. 14, 3632 (2012).
23. N. Matsumoto, T. Tsujimoto, A. Nakazaki, M. Isobe, T. Nishikawa, RSC Adv. 2, 9448 (2012).
24. S. Lou, B. M. Taoka, A. Ting, S. E. Schaus, J. Am. Chem. Soc. 127, 11256 (2005).
25. A. Ting, S. Lou, S. E. Schaus, Org. Lett. 8, 2003 (2006).
26. For details, please refer to the supplementary materials on Science Online.
27. Y. Li, J.-P. Feng, W.-H. Wang, J. Chen, X.-P. Cao, J. Org. Chem. 72, 2344 (2007).
28. B. M. Trost, C. D. Haffner, D. J. Jebaratnam, M. J. Krische, A. P. Thomas, J. Am. Chem. Soc. 121, 6183 (1999).
29. J. M. J. Verlaak, A. J. H. Klunder, B. Zwanenburg, Tetrahedron Lett. 23, 5463 (1982).
30. L. Shi, K. Meyer, M. F. Greaney, Angew. Chem. Int. Ed. 49, 9250 (2010).
31. P. Serrano, A. Llebaria, A. Delgado, J. Org. Chem. 67, 7165 (2002).
32. W. M. Pearlman, Tetrahedron Lett. 8, 1663 (1967).