New two-step sequence involving a hetero-Diels-Alder and a nonphenolic oxidative coupling reaction: A convergent access to analogs of steganacin

Tetrahedron Letters

Volumn 52, Issue 14, 2011, Pages 1608-1611

  Laurent, Mathieu Y ^a   Stocker, Vivien ^a   Temgoua, Valéry Momo ^a   Dujardin, Gilles ^a   Dhal, Robert ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

Atroposelectivity; Biaryl coupling; Hetero Diels Alder; Lignan; Steganacin

Indexed keywords

ENAMINE; LIGNAN; STEGANACIN; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; CYCLOADDITION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

ALNUS;

EID: 79952362662     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.097     Document Type: Article

References (24)

1. For reviews about lignans, see: J.-Y. Pan, S.-L. Chen, M.-H. Yang, J. Wu, J. Sinkkonen, and K. Zou Nat. Prod. Rep. 26 2009 1251 1292
2. R.S. Ward Nat. Prod. Rep. 16 1999 75 96
3. D.C. Ayers, and J.D. Loike Lignans: Chemical, Biological and Clinical Properties 1990 University Press Cambridge, UK
4. For a recent review, see: M. Saleem, H.J. Kim, M.S. Ali, and Y.S. Lee Nat. Prod. Rep. 22 2005 696 716
5. C. Canel, R.M. Moraes, F.E. Dayan, and D. Ferreira Phytochemistry 54 2000 115 120
6. S.M. Kupchan, R.W. Britton, M.F. Ziegler, C.J. Gilmore, R.J. Restivo, and R.F. Bryan J. Am. Chem. Soc. 95 1973 1335 1336
7. R.W.-J. Wang, L.I. Rebhun, and S.M. Kupchan Cancer Res. 37 1977 3071 3079
8. For a review about chemistry of colchicine: T. Greaning, and H.-G. Schmalz Angew. Chem., Int. Ed. 43 2004 3230 3256
9. C. Keller-Juslén, M. Kuhn, A. von Wartburg, and H. Stähelin J. Med. Chem. 14 1971 936 940
10. J.-Y. Sanceau, R. Dhal, and E. Brown Nat. Prod. Rep. 1 1992 221 224
11. For a review about stereoselective synthesis of atropoisomeric compounds see: M.C. Kozlowski, B.J. Morgan, and E.C. Linton Chem. Soc. Rev. 38 2009 3193 3207
12. C. Gaulon, P. Gizecki, R. Dhal, and G. Dujardin Synlett 2002 952 956
13. C. Gaulon, R. Dhal, T. Chapin, V. Maisonneuve, and G. Dujardin J. Org. Chem. 69 2004 4192 4202
14. G. Dujardin, S. Rossignol, and E. Brown Synthesis 1998 763 770
15. L. Maingot, S. Leconte, I. Chataigner, A. Martel, and G. Dujardin Org. Lett. 11 2009 1619 1622
16. E. Brown, G. Dujardin, and M. Maudet Tetrahedron 53 1997 9679 9694
17. F. Gohier, K. Bouhadjera, D. Faye, C. Gaulon, V. Maisonneuve, G. Dujardin, and R. Dhal Org. Lett. 9 2007 211 214
18. J.S. Sawyer, and T.L. Macdonald Tetrahedron Lett. 29 1988 4839 4842
19. S.G. Davies, M.-S. Key, H. Rodriguez-Solla, H.J. Sanganee, E.D. Savory, and A.D. Smith Synlett 2003 1659 1662
20. T. Lu, Z. Song, and R.P. Hsung Org. Lett. 10 2008 541 544
21. C. Gaulon, R. Dhal, and G. Dujardin Synthesis 2003 2269 2272
22. D. Planchenault, R. Dhal, and J.-P. Robin Tetrahedron 49 1993 5823 5830
23. D. Planchenault, and R. Dhal Tetrahedron 51 1995 1395 1404
24. G. Besong, K. Jarowicki, P.J. Kocienski, E. Sliwinski, and F.T. Boyle Org. Biomol. Chem. 4 2006 2193 2207