Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent

Organic Letters

Volumn 13, Issue 15, 2011, Pages 4108-4111

  Ghosh, Arun K ^a   Cheng, Xu ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EXCIPIENT; MACROLIDE; ZAMPANOLIDE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; METABOLISM; MICROTUBULE; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; EXCIPIENTS; MACROLIDES; MICROTUBULES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79961087497     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201626h     Document Type: Article

References (35)

1. Pazdur, R.; Kudelka, A. P.; Kavanagh, J. J.; Cohen, P. R.; Raber, M. N. Cancer Treat. Rev. 1993, 19, 351-386
2. Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 277, 665-667
3. Mani, S.; Macapinlac, M. J.; Goel, S.; Verdier-Pinard, D.; Fojo, T.; Rothenberg, M.; Colevas, D. Anti-cancer Drugs 2004, 15, 553-558
4. Hamel, E.; Day, B. W.; Miller, J. H.; Jung, M. K.; Northcote, P. T.; Ghosh, A. K.; Curan, D. P.; Cushman, M.; Nicolaou, K. C.; Paterson, I.; Sorenson, E. J. Mol. Phamacol. 2006, 70, 1555-1564
5. Gapud, E. J.; Bai, R.; Ghosh, A. K.; Hamel, E. Mol. Pharmacol. 2004, 66, 113-121
6. Hood, K. A.; West, L. M.; Rouwe, B.; Northcote, P. T.; Berridge, M. V.; Wakefield, S. J.; Miller, J. H. Cancer Res. 2002, 62, 3356-3360
7. Field, J. J.; Singh, A. J.; Kanakkanthara, A.; Halafihi, T.; Northcote, P. T.; Miller, J. H. J. Med. Chem. 2009, 52, 7328-7332
8. Tanaka, J.; Higa, T. Tetrahedron Lett. 1996, 37, 5535-5538
9. Uenishi, J.; Iwamoto, T.; Tanaka, J. Org. Lett. 2009, 11, 3262-3265
10. Smith, A. B., III; Safonov, I. G.; Corbett, R. M. J. Am. Chem. Soc. 2001, 123, 12426-12427
11. Hoye, T. R.; Hu, M. J. Am. Chem. Soc. 2003, 125, 9576-9577
12. Cutignano, A.; Bruno, I.; Bifulco, G.; Casapullo, A.; Debitus, C.; Gomez-Paloma, L.; Riccio, R. Eur. J. Org. Chem. 2001, 775-778
13. Smith, A. B., III; Safonov, I. G.; Corbett, R. M. J. Am. Chem. Soc. 2002, 124, 11102-11113
14. Ding, F.; Jennings, M. P. Org. Lett. 2005, 7, 2321-2324
15. Aubele, D. L.; Wan, S.; Floreancig, P. E. Angew. Chem. 2005, 117, 3551-3554
16. Angew. Chem., Int. Ed. 2005, 44, 3485-3488.
17. Sanchez, C. C.; Keck, G. E. Org. Lett. 2005, 7, 3053-3056
18. Louis, I.; Hungerford, N. L.; Humphries, E. J.; McLeod, M. D. Org. Lett. 2006, 8, 1117-1120
19. Zurwerra, D.; Gertsch, J.; Altmann, K.-H. Org. Lett. 2010, 12, 2302-2305
20. Yun, S. Y.; Hansen, E. C.; Volchkov, I.; Cho, E. J.; Lo, W. Y.; Lee, D. Angew. Chem. 2010, 122, 4357-4359
21. Angew. Chem., Int. Ed. 2010, 49, 4261-4263.
22. Troast, D. M.; Yuan, J.; Porco, J. A., Jr. Adv. Synth. Catal. 2008, 350, 1701-1711
23. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629-631
24. Narayanan, B. A.; Bunnelle, W. H. Tetrahedron Lett. 1987, 28, 6261-6264
25. Hayashi, Y.; Mukaiyama, T. Chem. Lett. 1987, 1811-1814
26. Yu, B.; Jiang, T.; Li, J.; Su, Y.; Pan, X.; She, X. Org. Lett. 2009, 11, 3442-3445
27. Tu, W.; Liu, L.; Floreancig, P. E. Angew. Chem. 2008, 120, 4252-4255
28. Angew. Chem., Int. Ed. 2008, 47, 4184-4187.
29. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920-1923
30. Smith, A. B., III; Dong, S. Org. Lett. 2009, 11, 1099-1102
31. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370
32. Lei, B.; Fallis, A. G. Can. J. Chem. 1991, 69, 1450-1456
33. Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem. 2005, 117, 7590-7593
34. Angew. Chem. Int.Ed. 2005, 44, 7424-7427.
35. Akiyama, T. Chem. Rev. 2007, 107, 5744-5758