Tricyclic marine alkaloids: Synthetic approaches to cylindricines, lepadiformine, and fasicularin

Chimia

Volumn 60, Issue 3, 2006, Pages 131-141

  Schär, Pascal ^b   Cren, Sylvaine ^b   Renaud, Philippe ^a  

^a UNIVERSITY OF BERN   (Switzerland)

^b NONE

Author keywords

Alkaloids; Azaspirocycles; Natural products; Perhydroquinolines; Total synthesis

Indexed keywords

EID: 33645910540     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/000942906777674976     Document Type: Review

References (35)

1. The depicted atom-numbering does not correspond to the IUPAC recommendations but was adopted for commodity reasons and is used consistently throughout this text.
2. A.J. Blackman, C. Li, D.C.R. Hockless, B.W. Skelton, A.H. White, Tetrahedron 1993, 49, 8645.
3. A.J. Blackman, C. Li, Aust. J. Chem. 1994, 47, 1355.
4. A.J. Blackman, C. Li, Aust. J. Chem. 1995, 48, 955.
5. J.-F. Biard, S. Guyot, C. Roussakis, J.-F. Verbist, J. Vercauteren, J.F. Weber, K. Boukef, Tetrahedron Lett. 1994, 35, 2691.
6. A.D. Patil, A.J. Freyer, R. Reichwein, B. Carte, L.B. Killmer, L. Faucette, R.K. Johnson, D.J. Faulkner, Tetrahedron Lett. 1997, 38, 363.
7. G.A. Molander, M. Rönn, J. Org. Chem. 1999, 64, 5183.
8. M. Jugé, N. Grimaud, J.-F. Biard, M.-P. Sauviat, M. Nabil, J.-F. Verbist, J.-Y. Petit, Toxicon 2001, 39, 1231.
9. H. Abe, S. Aoyagi, C. Kibayashi, J. Amer. Chem. Soc. 2000, 122, 4583.
10. H. Abe, S. Aoyagi, C. Kibayashi, Angew. Chem. Int. Ed. 2002, 41, 3017.
11. P. Sun, C. Sun, S.M. Weinreb, J. Org. Chem. 2002, 67, 4337.
12. S. Dutta, H. Abe, S. Aoyagi, C. Kibayashi, K.S. Gates, J. Amer. Chem. Soc. 2005, 127, 15004.
13. S.M. Weinreb, Acc. Chem. Res. 2003, 36, 59.
14. C. Kibayashi, S. Aoyagi, H. Abe, Bull. Chem. Soc. Jp. 2003, 76, 2059.
15. B.B. Snider, T. Liu, J. Org. Chem. 1997, 62, 5630.
16. J.F. Liu, C.H. Heathcock, J. Org. Chem. 1999, 64, 8263.
17. B.M. Trost, M.T. Rudd, Org. Lett. 2003, 5, 4599.
18. W.H. Pearson, N.S. Barta, J.W. Kampf, Tetrahedron Lett. 1997, 38, 3369.
19. W.H. Pearson, Y. Ren, J. Org. Chem. 1999, 64, 688.
20. K.M. Werner, J.M. de los Santos, S.M. Weinreb, M. Shang, J. Org. Chem. 1999, 64, 686.
21. K.M. Werner, J.M. de los Santos, S.M. Weinreb, M. Shang, J. Org. Chem. 1999, 64, 4865.
22. T.J. Greshock, R.L. Funk, Org. Lett. 2001, 3, 3511.
23. J.-H. Maeng, R.L. Funk, Org. Lett. 2002, 4, 331.
24. B.E. Maryanoff, H.C. Zhang, J.H. Cohen, I.J. Turchi, C.A. Maryanoff, Chem. Rev. 2004, 104, 1431.
25. W.N. Speckamp, M.J. Moolenaar, Tetrahedron 2000, 56, 3817.
26. T. Arai, H. Abe, S. Aoyagi, C. Kibayashi, Tetrahedron Lett. 2004, 45, 5921.
27. P. Sun, C. Sun, S.M. Weinreb, Org. Lett. 2001, 3, 3507.
28. H. Abe, S. Aoyagi, C. Kibayashi, J. Amer. Chem. Soc. 2005, 127, 1473.
29. J. Liu, J.J. Swidorski, S.D. Peters, R.P. Hsung, J. Org. Chem. 2005, 70, 3898.
30. S. Canesi, D. Bouchu, M.A. Ciufolini, Angew. Chem. Int. Ed. 2004, 43, 4336.
31. M.D.B. Fenster, G.R. Dake, Chem. Eur. J. 2005, 11, 639.
32. P. Renaud, C. Ollivier, P. Panchaud, Angew. Chem. Int. Ed. 2002, 41, 3460.
33. P. Panchaud, C. Ollivier, P. Renaud, S. Zigmantas, J. Org. Chem. 2004, 69, 2755.
34. P. Panchaud, L. Chabaud, Y. Landais, C. Ollivier, P. Renaud, S. Zigmantas, Chem. Eur. J. 2004, 10, 3606.
35. P. Schär, P. Renaud, Org. Lett. 2006, 8, in press.