Sequential sonagashira and larock indole synthesis reactions in a general strategy to prepare biologically active β-carboline-containing alkaloids

Organic Letters

Volumn 16, Issue 23, 2014, Pages 6124-6127

  Pan, Xiaohong ^a   Bannister, Thomas D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; CARBOLINE DERIVATIVE; INDOLE ALKALOID; PALLADIUM;

CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; CARBOLINES; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 84916214276     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5029783     Document Type: Article

References (27)

1. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875-2911
2. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690
3. Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662
4. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470
5. Chinchilla, R.; Nájera, C. Chem. Soc. Rev. 2011, 40, 5084-5121
6. Shen, M.; Li, G.; Lu, B. Z.; Hossain, F. A.; Roschangar, F.; Farina, V.; Senanayake, C. H. Org. Lett. 2005, 6, 4129-4132
7. Li, G.; Liu, J.; Lu, B.; Roschangar, F.; Senanayake, C. H.; Shen, M. (2005, U.S. Patent 20,050,209,465.
8. Gribble, G. W.; Johnson, D. A. Tetrahedron Lett. 1987, 28, 5259-5262
9. Gribble, G. W.; Barden, T. C.; Johnson, D. A. Tetrahedron 1988, 44, 3195-3202
10. Fürstner, A.; Ernst, A.; Krause, H.; Ptock, A. Tetrahedron 1996, 52, 7329-7344
11. Fürstner, A.; Ernst, A. Tetrahedron 1995, 51, 773-786
12. Gribble, G. W. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1988; Vol. 1, p 123.
13. Britton, T. C.; Dehlinger, V.; Dell, P. C.; Dressman, B. A.; Myers, J. K.; Nisenbaum, S. E. (2006, PCT Int. Appl. WO 2006/0444554 A1.
14. Chatterjee, A.; Ghosh, S. Synthesis 1981, 10, 818-20
15. Knölker, H.-J.; Cämmerer, S. Tetrahedron Lett. 2000, 41, 5035-5038
16. Eastwood, P. R.; Gonzalez, J. R.; Bach, T. J.; Santacana, L. M. P.; Moll, J. T.; Javaloyes, J. F. C.; Matassa, V. G. (2011, PCT Int. Appl. WO 2011/076419 A1.
17. Manna, R. K.; Jaisankar, P.; Giri, V. S. Synth. Commun. 1995, 25, 3027-3034
18. Xu, X.-Y.; Yang, X.-H.; Li, S.-Z.; Song, Q.-S. Helv. Chim. Acta 2011, 94, 1470-1476
19. Stoit, A. S.; Pandit, U. K. Heterocycles 1987, 25, 7-10
20. Koike, K.; Ohmoto, T.; Uchida, A.; Oonishi, I. Heterocycles 1994, 38, 1413-1420
21. Dyker, G.; Hildebrandt, D. J. Org. Chem. 2005, 70, 6093-6096
22. Manna, R. K.; Jaisankar, P.; Giri, V. S. J. Chem. Res., Synop. 1999, 350-351
23. Peng, S.; Zhang, L.; Cai, M.; Winterfeldt, E. Liebigs Ann. Chem. 1993, 141-146
24. Takayama, H.; Maeda, M.; Ohbayashi, S.; Kitajima, M.; Sakai, S-i.; Aimi, N. Tetrahedron Lett. 1995, 36, 9337-9340
25. Ma, J.; Yin, W.; Zhou, H.; Cook, J. M. Org. Lett. 2007, 9, 3491-3494
26. Kerschgens, I. P.; Claveau, E.; Wanner, M. J.; Ingemann, S.; van Maarseveen, J. H.; Hiemstra, H. Chem. Commun. 2012, 48, 12243-12245
27. Matsumoto, K.; Takayama, H.; Ishikawa, H.; Aimi, N.; Ponglux, D.; Watanabe, K.; Horie, S. Life Sci. 2006, 78, 2265-2271