Total synthesis of microtubule-stabilizing agent ceratamine A

Journal of Organic Chemistry

Volumn 78, Issue 24, 2013, Pages 12814-12818

  Feng, Qiguo ^a   Tao, Lulu ^a   Liu, Zhanzhu ^a  

^a PEKING UNION MEDICAL COLLEGE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; CELLULAR EFFECTS; SCHMIDT; SIDE-CHAINS; TOTAL SYNTHESIS;

CHEMISTRY; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

5 METHOXYBENZIMIDAZOLE; ALKALOID DERIVATIVE; ANTIMITOTIC AGENT; BENZIMIDAZOLE DERIVATIVE; CERATAMINE A; LACTAM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BENZYLATION; DEHYDROGENATION; DRUG SYNTHESIS; HYDROLYSIS; METHYLATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

ANIMALS; AZEPINES; IMIDAZOLES; MICROTUBULES; MOLECULAR STRUCTURE; PORIFERA; STEREOISOMERISM;

EID: 84890914023     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402165n     Document Type: Article

References (29)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327
2. Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 277, 665-667
3. Rowinsky, E. K. Annu. Rev. Med. 1997, 48, 353-374
4. Jordan, M. A.; Wilson, L. Nat. Rev. Cancer 2004, 4, 253-265
5. Kuppens, I. E. L. M. Curr. Clin. Pharmacol. 2006, 1, 57-70
6. Donovan, D.; Vahdat, L. T. Oncology 2008, 22, 408-416
7. Manzo, E.; van Soest, R.; Matainaho, L.; Roberge, M.; Andersen, R. J. Org. Lett. 2003, 5, 4591-4594
8. Karjala, G.; Chan, Q.; Manzo, E.; Andersen, R. J.; Roberge, M. Cancer Res. 2005, 65, 3040-3043
9. Nodwell, M.; Riffell, J. L.; Roberge, M.; Andersen, R. J. Org. Lett. 2008, 10, 1051-1054
10. Nodwell, M.; Pereira, A.; Riffell, J. L.; Zimmerman, C.; Patrick, B. O.; Roberge, M.; Andersen, R. J. J. Org. Chem. 2009, 74, 995-1006
11. Coleman, R. S.; Campbell, E. L.; Carper, D. J. Org. Lett. 2009, 11, 2133-2136
12. Nodwell, M.; Zimmerman, C.; Roberge, M.; Andersen, R. J. J. Med. Chem. 2010, 53, 7843-7851
13. Scarponi, U.; Cimaschi, R.; Rusconi, L.; Santangelo, F.; Arcari, G. Farmaco, Ed. Sci. 1985, 40, 818-832
14. Zlotos, D. P.; Meise, W. Heterocycles 1997, 45, 2137-2157
15. Dalence-Guzman, M. F.; Berglund, M.; Skogvall, S.; Sterner, O. Bioorg. Med. Chem. 2008, 16, 2499-2512
16. Zuev, D.; Michne, J. A.; Huang, H.; Beno, B. R.; Wu, D.; Gao, Q.; Torrente, J. R.; Xu, C.; Conway, C. M.; Macor, J. E.; Dubowchik, G. M. Org. Lett. 2005, 7, 2465-2468
17. Sun, C.; Lin, X.; Weinreb, S. M. J. Org. Chem. 2006, 71, 3159-3166
18. Plante, J. P.; Glass, T. E. Org. Lett. 2006, 8, 2163-2166
19. Verma, S. K.; Acharya, B. N.; Kaushik, M. P. Org. Biomol. Chem. 2011, 9, 1324-1327
20. Ognyanov, V. I.; Balan, C.; Bannon, A. W.; Bo, Y.; Dominguez, C.; Fotsch, C.; Gore, V. K.; Klionsky, L.; Ma, Vu. V.; Qian, Y. X.; Tamir, R. J. Med. Chem. 2006, 49, 3719-3742
21. Whittle, C. P. Aust. J. Chem. 1980, 33, 1545-1551
22. Hartwig, J. F.; Hooper, M. W.; Utaunomiya, M. J. Org. Chem. 2003, 68, 2861-2873
23. Hong, Y.; Tanoury, G. J.; Wilkinson, H. S.; Bakale, R. P.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 1997, 38, 5607-5610
24. Rosenberg, A. J.; Clark, D. A. Org. Lett. 2012, 14, 4678-4681
25. Beccalli, E. M.; Clerici, F.; Marchesini, A. Tertahedron 2000, 56, 2699-2702
26. Huffman, J. W.; Wu, M. J.; Lu, J. J. Org. Chem. 1998, 63, 4510-4514
27. Rosenberg, A. J.; Zhao, J.; Clark, D. A. Org. Lett. 2012, 14, 1764-1767
28. Clark, D. A.; Rosenberg, A. J.; Williams, T. M.; Jordan, A. J. Org. Biomol. Chem. 2013, 11, 3064-3072
29. Robins, M. J.; Hatfield, P. W.; Balzarini, J.; Clercq, E. D. J. Med. Chem. 1984, 27, 1486-1492