Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction

Organic Letters

Volumn 12, Issue 16, 2010, Pages 3708-3711

  Xu, Jing ^a   Caro Diaz, Eduardo J E ^a   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ENGLERIN A; ENGLERIN B; FURAN DERIVATIVE; RHODIUM; SESQUITERPENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CATALYSIS; CYCLIZATION; FURANS; MOLECULAR STRUCTURE; RHODIUM; SESQUITERPENES, GUAIANE; STEREOISOMERISM;

EID: 77955683809     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1015652     Document Type: Article

References (26)

1. Jemal, A.; Siegel, R.; Ward, E.; Hao, Y.; Xu, J.; Thun, M. J. Cancer Statistics 2009 CA Cancer J. Clin. 2009, 59, 225-249
2. Ratnayake, R.; Covell, D.; Ransom, T. T.; Gustafson, K. R.; Beutler, J. A. Org. Lett. 2009, 11, 57-60
3. Beutler, J. A.; Ratnayake, R.; Covell, D.; Johnson, T. R. WO 2009/088854, 2009.
4. Peng, G.-P.; Tian, G.; Huang, X.-F.; Lou, F.-C. Phytochemistry 2003, 63, 877-881
5. Huang, S.-X.; Yang, J.; Xiao, W.-L.; Zhu, Y.-L.; Li, R.-T.; Li, L.-M.; Pu, J.-X.; Li, X.; Li, S.-H.; Sun, H.-D. Helv. Chim. Acta 2006, 89, 1169-1175
6. Willot, M.; Radtke, L.; Könning, D.; Fröhlich, R.; Gessner, V. H.; Strohmann, C.; Christmann, M. Angew. Chem., Int. Ed. 2009, 48, 9105-9108
7. Zhou, Q.-F.; Chen, X.-F.; Ma, D.-W. Angew. Chem., Int. Ed. 2010, 49, 3513-3516
8. Molawi, K.; Delpont, N.; Echavarren, A. M. Angew. Chem., Int. Ed. 2010, 49, 3517-3519
9. Nicolaou, K. C.; Kang, Q.; Ng, S. Y.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 8219-8222
10. Jiménez-Núñez, E.; Claverie, C. K.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 5452-5455
11. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2009, 45, 7327-7329
12. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10782
13. For an excellent review, see: Jeong, N.; Robinson, J. E.; Wender, P. A.; Gamber, G. G.; Williams, T. J.; Davies, H. M. L.; Walji, A. M. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005; Chapters 11-14, pp 215 -340.
14. For a recent application of this strategy on natural product synthesis, see also: Jackson, K. L.; Henderson, J. A.; Motoyoshi, H.; Phillips, A. J. Angew. Chem., Int. Ed. 2009, 48, 2346-2350
15. Weyerstahl, P.; Brendel, J. Liebigs Ann. Chem. 1988, 1015-1016
16. 1H NMR spectroscopy.
17. Poirier, J.-M.; Hennequin, L. Tetrahedron 1989, 45, 4191-4202
18. Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241-3243
19. Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 15, 4319-4322
20. CCDC782508 contains the supplementary crystallographic data for compound 13. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/products/csd/request/.
21. Hooft, W. W. R.; Straver, L. H.; Spek, A. L. J. Appl. Crystallogr. 2008, 41, 96-103
22. Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647
23. To our surprise, compared to regular intramolecular reactions, this intramolecular aldol reaction requires quite high concentration (0.4-0.7 M).
24. 2.
25. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 16, 1574-1585
26. Atkins, G. M.; Burgess, E. M. J. Am. Chem. Soc. 1968, 90, 4744-4745