Total synthesis of the antibiotic Elansolid B1

Organic Letters

Volumn 16, Issue 2, 2014, Pages 568-571

  Weber, Arne ^a   Dehn, Richard ^a   Schläger, Nadin ^a   Dieter, Bastian ^a   Kirschning, Andreas ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; ELANSOLID B1; MACROLIDE;

ARTICLE; BIOMIMETICS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BIOMIMETICS; MACROLIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84896759510     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403441c     Document Type: Article

References (33)

1. Gerth, K.; Steimetz, H.; Höfle, G. EP 2093212 A1, 2009.
2. Steinmetz, H.; Gerth, K.; Jansen, R.; Schläger, N.; Dehn, R.; Reinecke, S.; Kirschning, A.; Müller, R. Angew. Chem. 2011, 123, 553-557;
3. Angew Chem., Int. Ed. 2011, 50, 532-536.
4. Steinmetz, H.; Zander, Z.; Shushni, M. A. M.; Jansen, R.; Gerth, K.; Dehn, R.; Dräger, G.; Kirschning, A.; Müller, R. ChemBioChem 2012, 13, 1813-1817.
5. Jansen, R.; Gerth, K.; Steinmetz, H.; Reinecke, S.; Kessler, W.; Kirschning, A.; Müller, R. Chem.-Eur. J. 2011, 17, 7739-7744.
6. Dehn, R.; Katsuyama, Y.; Weber, A.; Gerth, K.; Jansen, R.; Steinmetz, H.; Höfle, G.; Müller, R.; Kirschning, A. Angew. Chem. 2011, 123, 3968-3973
7. Angew. Chem., Int. Ed. 2011, 50, 3882-3887.
8. Inagaki, M.; Haga, N.; Kobayashi, M.; Ohta, N.; Kamata, S.; Tsuri, T. J. Org. Chem. 2002, 67, 125-128.
9. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1989, 111, 1136-1138.
10. So far, only simpler examples without the presence of neighboring quarternary centers have been reported: (a) Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, P. D.; Williams, D. J. J. Org. Chem. 1984, 84, 3503-3516.
11. Roush, W. R. J. Am. Chem. Soc. 1980, 102, 1390-1404.
12. Saito, S.; Shiozawa, M.; Yamamoto, H. Angew. Chem. 1999, 111, 1884-1886
13. Angew. Chem., Int. Ed. 1999, 38, 1769-1771.
14. Saito, S.; Yamamoto, H. Chem. Commun. 1997, 1585-1592.
15. Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem. 2001, 113, 623-627
16. Angew. Chem., Int. Ed. 2001, 40, 603-607.
17. Abramite, J. A.; Sammakia, T. Org. Lett. 2007, 9, 2103-2106.
18. Schläger, N.; Kirschning, A. Org. Biomol. Chem. 2012, 10, 7721-7729.
19. Ley, S. V.; Norman, L.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
20. Ihara, H.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 7502-7503.
21. Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861-2863.
22. Brown, H. C.; Cho, B. T.; Park, W. C. J. Org. Chem. 1988, 53, 1231-1238.
23. Lundgren, R. L.; Stradiotto, M. Chem.-Eur. J. 2008, 14, 10388-10395.
24. Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, 6716-6717.
25. Lee, S. J.; Gray, K. C.; Paek, J. S.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 466-468.
26. Use of MIDA building blocks in total syntheses: (a) Fuji, S.; Chang, S. Y.; Burke, M. D. Angew. Chem. 2011, 123, 8008-8010;
27. Angew. Chem., Int. Ed. 2011, 50, 7862-7864.
28. Fijita, K.; Matsui, R.; Suzuki, T.; Kobayashi, S. Angew. Chem. 2012, 124, 7383-7386;
29. Angew. Chem., Int. Ed. 2012, 51, 7271-7274.
30. Oger, C.; Balas, L.; Durand, T.; Galano, J.-M. Chem. Rev. 2013, 113, 1313-1350.
31. Myers, A. G.; Zheng, B.; Movassaghi, M. J. Org. Chem. 1997, 62, 7507-7507.
32. Whittaker, A. M.; Lalic, G. Org. Lett. 2013, 15, 1112-1115.
33. Boland, W.; Schroer, N.; Sieler, C.; Feigel, M. Helv. Chim. Acta 1987, 70, 1025-1040.