Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction

Journal of the American Chemical Society

Volumn 132, Issue 23, 2010, Pages 7870-7871

  Pathak, Tejas P ^a   Gligorich, Keith M ^b   Welm, Bryan E ^b   Sigman, Matthew S ^a,b  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF UTAH SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTICANCER ACTIVITIES; BIOLOGICAL STUDIES; DIFUNCTIONALIZATION; ENANTIOSELECTIVE; MCF-7 CELLS; MOLECULAR COMPLEXITY; RAPID CONSTRUCTION; SUBSTITUTED INDOLES;

OLEFINS; PALLADIUM;

SYNTHESIS (CHEMICAL);

ALKENE; ANTINEOPLASTIC AGENT; INDOLE DERIVATIVE; PALLADIUM;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CELL STRAIN MCF 7; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY;

ALKENES; ANTINEOPLASTIC AGENTS; CATALYSIS; CELL LINE, TUMOR; HUMANS; INDOLES; INHIBITORY CONCENTRATION 50; PALLADIUM; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 77953298188     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103472a     Document Type: Article

References (20)

1. Atta-ur-Rahman Basha, A. Indole Alkaloids; Harwood Academic: Chichester, U.K., 1998.
2. Kutney, J. P. The Synthesis of Indole Alkaloids. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley-Interscience: New York, 1977; Vol. 3, p 273.
3. Somai, M. and Yamada, F. Nat. Prod. Rep. 2005, 22, 73
4. Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Ress, C. W., Scriven, E. F. V., and Bird, C. W., Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 2, p 119.
5. Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Ress, C. W., Scriven, E. F. V., and Bird, C. W., Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 2, p 207.
6. Indoles; Sundberg, R. J., Ed.; Academic Press: London, 1996.
7. For recent reviews of the use of indoles in enantioselective catalysis, see: Bandini, M., Melloni, A., Tommasi, S., and Umani-Ronchi, A. Synlett 2005, 1199
8. Joucla, L. and Djakovitch, L. Adv. Synth. Catal 2009, 351, 673
9. Bandini, M. and Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
10. Jensen, K. H., Pathak, T. P., Zhang, Y., and Sigman, M. S. J. Am. Chem. Soc. 2009, 131, 17074
11. For the reaction of indoles with quinone methides, see: Decodts, G., Wakselman, M., and Vikas, M. Tetrahedron 1970, 26, 3313
12. Spande, T. F., Wilchek, M., and Witkpo, B. J. Am. Chem. Soc. 1968, 90, 3256
13. McFarland, B. G., Inoue, Y., and Nakanishi, K. Tetrahedron Lett. 1969, 10, 857
14. Yang, S.-D., Sun, C.-L., Fang, Z., Li, B.-J., Li, Y.-Z., and Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1473
15. See the Supporting Information for more details.
16. See the Table 1 footnote for detailed optimized conditions.
17. Kamenecka, M. T. and Danishefsky, S. J. Chem. - Eur. J. 2001, 7, 41
18. Schwaebisch, D., Tchabanenko, K., Adlington, R. M., Cowley, A. M., and Baldwin, J. E. Chem. Commun. 2004, 2552
19. The diastereomers were readily separated.
20. Siengalewicz, P., Gaich, T., and Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 8170