Model studies on the synthesis of madangamine alkaloids. Assembly of the macrocyclic rings

Organic Letters

Volumn 14, Issue 15, 2012, Pages 3916-3919

  Proto, Stefano ^a   Amat, Mercedes ^a   Pérez, Maria ^a   Ballette, Roberto ^a   Romagnoli, Federica ^a   Mancinelli, Andrea ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; FUSED HETEROCYCLIC RINGS; MADANGAMINE A;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84864625032     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301672y     Document Type: Article

References (27)

1. Andersen, R. J.; van Soest, R. W. M.; Kong, F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, U. K., 1996; Vol. 10, pp 301-355.
2. Berlinck, R. G. S. Top Heterocycl. Chem. 2007, 10, 211-238
3. Kornprobst, J.-M. Encyclopedia of Marine Natural Products; Wiley: Weinheim, 2010; Vol. 2, pp 683-723.
4. Kong, F.; Andersen, R. J.; Allen, T. M. J. Am. Chem. Soc. 1994, 116, 6007-6008
5. Kong, F.; Graziani, E. I.; Andersen, R. J. J. Nat. Prod. 1998, 61, 267-271
6. de Oliveira, J. H. H. L.; Nascimento, A. M.; Kossuga, M. H.; Cavalcanti, B. C.; Pessoa, C. O.; Moraes, M. O.; Macedo, M. L.; Ferreira, A. G.; Hajdu, E.; Pinheiro, U. S.; Berlinck, R. G. S. J. Nat. Prod. 2007, 70, 538-543
7. Matzanke, N.; Gregg, R. J.; Weinreb, S. M. J. Org. Chem. 1997, 62, 1920-1921
8. Yamazaki, N.; Kusanagi, T.; Kibayashi, C. Tetrahedron Lett. 2004, 45, 6509-6512
9. Yoshimura, Y.; Kusanagi, T.; Kibayashi, C.; Yamazaki, N.; Aoyagi, S. Heterocycles 2008, 75, 1329-1354
10. Tong, H. M.; Martin, M.-T.; Chiaroni, A.; Bénéchie, M.; Marazano, C. Org. Lett. 2005, 7, 2437-2440
11. Quirante, J.; Paloma, L.; Diaba, F.; Vila, X.; Bonjoch, J. J. Org. Chem. 2008, 73, 768-771
12. Amat, M.; Pérez, M.; Proto, S.; Gatti, T.; Bosch, J. Chem.-Eur. J. 2010, 16, 9438-9441
13. Meng, Q.; Hesse, M. Top. Curr. Chem. 1991, 161, 109-176
14. Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238
15. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527
16. Gradillas, A.; Pérez-Castells, J. Angew. Chem., Int. Ed. 2006, 45, 6068-6101
17. Dutheuil, G.; Webster, M. P.; Worthington, P. A.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2009, 48, 6317-6319
18. Gueugnot, S.; Aiami, M.; Linstrumeile, G.; Mambu, L.; Petit, Y.; Larchevêque, M. Tetrahedron 1996, 52, 6635-6646
19. For a review on the construction of (Z, Z) skipped 1,4-dienes, see: Durand, S.; Parrain, J.-L.; Santelli, M. J. Chem. Soc., Perkin Trans. 1 2000, 253-273
20. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408
21. Yoshimura, Y.; Inoue, J.; Yamazaki, N.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2006, 47, 3489-3492
22. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186
23. Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509-6512
24. Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1-157
25. Zamboni, R.; Milette, S.; Rokach, J. Tetrahedron Lett. 1983, 24, 4899-4902
26. Wang, S. S.; Rokach, J.; Powell, W. S.; Dekle, C.; Feinmark, S. J. Tetrahedron Lett. 1994, 35, 4051-4054
27. Sandri, J.; Viala, J. J. Org. Chem. 1995, 60, 6627-6630