Enantioselective synthesis of glutarimide alkaloids cordiarimides A, B, crotonimides A, B, and julocrotine

Chinese Journal of Chemistry

Volumn 29, Issue 7, 2011, Pages 1312-1318

  Teng, Bo ^a   Zheng, Jianfeng ^a   Huang, Huiying ^a   Huang, Peiqiang ^a  

^a XIAMEN UNIVERSITY   (China)

Author keywords

alkaloids; asymmetric hydrogenation; diastereoselectivity; enantioselective synthesis; glutarimides

Indexed keywords

EID: 79960942888     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201180248     Document Type: Article

References (45)

1. Chen, M.,;, Doherty, S. D.,;, Hsu, S.,. Dermatol. Clin., 2010, 28, 577.
2. Kathrin, S.,;, Heinz, L.,. Blood Rev., 2002, 16, 207.
3. Singhal, S.,;, Mehta, J.,. Biomed. Pharmacother., 2002, 56, 4.
4. Li, Q. B.,;, Fang, H.,;, Xu, W. F.,. Bioorg. Med. Chem. Lett., 2007, 17, 2935.
5. Li, Q. B.,;, Fang, H.,;, Wang, X. J.,;, Xu, W. F.,. Eur. J. Med. Chem., 2010, 45, 1618.
6. Cui, S. X.,;, Qu, X. J.,;, Gao, Z. H.,;, Zhang, Y. S.,;, Zhang, X. F.,;, Zhao, C. R.,;, Xu, F. W.,;, Li, Q. B.,;, Han, J. X.,. Cancer Lett., 2010, 28, 153.
7. Inagaki, Y.,;, Tang, W.,;, Zhang, L.,;, Du, G. H.,;, Xu, W. F.,;, Kokudo, N.,. Biosci. Trends, 2010, 4, 56.
8. Zhang, X. P.,;, Fang, H.,;, Zhu, H. W.,;, Wang, X. J.,;, Zhang, L.,;, Li, M. Y.,;, Li, Q. B.,;, Yuan, Y. M.,;, Xu, W. F.,. Bioorg. Med. Chem., 2010, 18, 5981.
9. Nakano, T.,;, Djerassi, C.,;, Corral, R. A.,;, Orazi, O. O.,. J. Org. Chem., 1961, 26, 1184.
10. Anastasi, C.,. Anales. Asoc. Quim. Argent., 1925, 13, 348.
11. Aboagye, F. A.,;, Sam, G. H.,;, Massiot, G.,;, Lavaud, C.,. Fitoterapia, 2000, 71, 461.
12. Moreira, R. Y. O.,;, Brasil, D. S. B.,;, Alves, C. N.,;, Guilhon, G. M.,;, Santos, L. S.,;, Arruda, M. S. P.,. Int. J. Quantum. Chem., 2008, 108, 513.
13. Suarez, A. I.,;, Blanco, Z.,;, Delle Monache, F.,;, Compagnone, R. S.,;, Arvelo, F.,. Nat. Prod. Res., 2004, 18, 421.
14. Barbosa, P. S.,;, Abreu, A. S.,;, Batista, E. F.,;, Guilhon, G. M. S. P.,;, Müller, A. H.,;, Arruda, M. S. P.,;, Santos, L. S.,;, Arruda, A. C.,;, Secco, R. S.,. Biochem. Syst. Ecol., 2007, 35, 887.
15. Kutney, J. P.,;, Klein, F. K.,;, Eigendorf, G.,;, McNeill, D.,;, Stuart, K. L.,. Tetrahedron Lett., 1971, 12, 4973.
16. Stuart, K. L.,;, McNeill, D.,;, Kutney, J. P.,;, Eigendorf, G.,;, Klein, P. K.,. Tetrahedron, 1973, 29, 4071.
17. Parks, J.,;, Gyeltshen, T.,;, Prachyawarakorn, V.,;, Mahidol, C.,;, Ruchirawat, S.,;, Kittakoop, P.,. J. Nat. Prod., 2010, 73, 992.
18. Huang, P.-Q.,. Synlett, 2006, 1133.
19. Huang, P.-Q.,;, Fu, R.,;, Ye, J.-L.,;, Dai, X.-J.,;, Ruan, Y.-P.,. J. Org. Chem., 2010, 75, 4230.
20. Huang, P.-Q.,;, Yang, R.-F.,. Chem. Eur. J., 2010, 16, 10319.
21. Huang, P.-Q.,;, Liu, W.-J.,;, Ye, J.-L.,. Org. Biomol. Chem., 2010, 8, 2085.
22. Luzzio, F. A.,;, Mayorov, A. V.,;, Ng, S. S.,;, Kruger, E. A.,;, Figg, W. D.,. J. Med. Chem., 2003, 46, 3793.
23. Zhu, X. X.,;, Giordano, T.,;, Yu, Q.-S.,;, Holloway, H. W.,;, Perry, T. A.,;, Lahiri, D. K.,;, Brossi, A.,;, Gerig, N. H.,. J. Med. Chem., 2003, 46, 5222.
24. Capitosti, S. M.,;, Hansen, T. P.,;, Brown, M. L.,. Org. Lett., 2003, 16, 2865.
25. Nakamura, T.,;, Noguchi, T.,;, Kobayashi, H.,;, Miachi, H.,;, Hashimoto, Y.,. Chem. Pharm. Bull., 2006, 54, 1709.
26. Robin, S. R.,;, Zhu, J. R.,;, Galons, H.,;, Pham-Huy, C.,;, Claude, J. R.,;, Tomas, A.,;, Viossat, B.,. Tetrahedron: Asymmetry, 1995, 6, 1249.
27. Estiarte, M. A.,;, de Souza, M. V. N.,;, del Rio, X.,;, Dodd, R. H.,;, Diez, A.,. Tetrahedron, 1999, 55, 10173.
28. Ostendorf, M.,;, Romagnoli, R.,;, Cabeza Pereiro, I.,;, Roos, E. C.,;, Moolenaar, M. J.,;, Speckamp, W. N.,;, Hiemstra, H.,. Tetrahedron: Asymmetry, 1997, 8, 1773.
29. Romagnoli, R.,;, Roos, E. C.,;, Hiemstra, H.,;, Moolenaar, M. J.,;, Speckamp, W. N.,. Tetrahedron Lett., 1994, 35, 1087.
30. Wang, Y.-Q.,;, Lu, S.-M.,;, Zhou, Y.-G.,. Org. Lett., 2005, 7, 3235.
31. Glorius, F.,;, Spielkamp, N.,;, Holle, S.,;, Goddard, R.,;, Lehmann, C. W.,. Angew. Chem., Int. Ed., 2004, 43, 2850.
32. Mhadgut, S. C.,;, Bucsi, I.,;, Toeroek, M.,;, Toeroek, B.,. Chem. Commum., 2004, 984.
33. Wang, D.-S.,;, Chen, Q.-A.,;, Li, W.,;, Yu, C.-B.,;, Zhou, Y.-G.,;, Zhang, X. M.,. J. Am. Chem. Soc., 2010, 132, 8909.
34. Chen, M.-W.,;, Duan, Y.,;, Chen, Q.-A.,;, Wang, D.-S.,;, Yu, C.-B.,;, Zhou, Y.-G.,. Org. Lett., 2010, 12, 5075.
35. Yang, Q.,;, Shang, G.,;, Gao, W. Z.,;, Deng, J. G.,;, Zhang, X. M.,. Angew. Chem., Int. Ed., 2006, 45, 3832.
36. Corey, E. J.,;, Helal, C. J.,. Angew. Chem., Int. Ed., 1998, 37, 1986.
37. Delous, L.,;, Srebnik, M.,. Chem. Rev., 1993, 93, 763.
38. Wallbaum, S.,;, Martens, J.,. Tetrahedron: Asymmetry, 1992, 3, 1475.
39. Corey, E. J.,;, Bakshi, R. K.,;, Shibata, S.,;, Chen, C.-P.,;, Singh, V. K.,. J. Am. Chem. Soc., 1987, 109, 7925.
40. Ager, D. J.,;, Laneman, S. A.,. Tetrahedron: Asymmetry, 1997, 8, 3327.
41. Noyori, R.,;, Hashiguchi, S., Acc. Chem. Res, 1997, 30, 97.
42. Noyori, R.,;, Ohkuma, T.,. Angew. Chem., Int. Ed., 2001, 40, 40.
43. Noyori, R.,. Angew. Chem., Int. Ed., 2002, 41, 2008.
44. Kumara Swamy, K. C.,;, Bhuvan Kumar, N. N.,;, Balaraman, E.,;, Pavan Kumar, K. V. P.,. Chem. Rev., 2009, 109, 2551.
45. Walker, M. A.,. J. Org. Chem., 1995, 60, 5352.