Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols

Tetrahedron

Volumn 68, Issue 20, 2012, Pages 3899-3907

  Chalal, Malik ^a   Vervandier Fasseur, Dominique ^a   Meunier, Philippe ^a   Cattey, Hélène ^a   Hierso, Jean Cyrille ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

Ferrocenyl phosphane; Heck coupling; Hydroxylated stilbenes; Protective group; Wittig reaction

Indexed keywords

CARBON DIOXIDE; CARBONIC ACID DERIVATIVE; ETHYLENE DERIVATIVE; FERROCENE DERIVATIVE; FUNCTIONAL GROUP; LIGAND; PALLADIUM; PHENOL DERIVATIVE; PHOSPHINE DERIVATIVE; REAGENT; RESVERATROL; STILBENE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; DEPROTECTION REACTION; HECK REACTION; HYDROXYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; WITTIG REACTION;

EID: 84859793294     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.025     Document Type: Article

References (41)

1. Burns, J.; Yokota, T.; Ashihara, H.; Lean, M. E. J.; Crozier, A. J. Agric. Food Chem. 2002, 50, 3337.
2. Stef, G.; Csiszar, A.; Lerea, K.; Ungvari, Z.; Veress, G. J. Cardiovasc. Pharmacol. 2006, 48, 1.
3. Latruffe, N.; Delmas, D.; Lizard, G.; Tringali, C.; Spatafora, C.; Vervandier-Fasseur, D.; Meunier, P. In Bioactive Compounds from Natural Sources - 2nd Ed.: Natural Products as Lead Compounds in Drug Discovery; Corrado, T., Ed.; Taylor & Francis Group: Boca Raton, Florida, 2011; pp 339-378.
4. (a) Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W. W.; Fong, H. H. S.; Farnsworth, N. R.; Kinghorn, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Science 1997, 275, 218;
5. (b) Lee, H. J.; Seo, J. W.; Lee, B. H.; Chung, K.-H.; Chi, D. Y. Bioorg. Med. Chem. Lett. 2004, 14, 463;
6. (c) de Medina, P.; Casper, R.; Savouret, J.-F.; Poirot, M. J. Med. Chem. 2005, 48, 287;
7. (d) Li, Y.-Q.; Li, Z.-L.; Zhao, W.-J.; Wen, R.-X.; Meng, Q.-W.; Zeng, Y. Eur. J. Med. Chem. 2006, 41, 1084.
8. Matsuda, H.; Morikawa, T.; Toguchida, I.; Park, J.-Y.; Harima, S.; Yoshikawa, M. Bioorg. Med. Chem. 2001, 9, 41.
9. Izard, J.-C.; Fourneron, J.-D. FR 9910904, 1999.
10. Jeffrey, J. L.; Sarpong, R. Org. Lett. 2009, 11, 5450.
11. Mazué, F.; Colin, D.; Gobbo, J.; Wegner, M.; Rescifina, A.; Spatafora, C.; Fasseur, D.; Delmas, D.; Meunier, P.; Tringali, C.; Latruffe, N. Eur. J. Med. Chem. 2010, 45, 2972.
12. (a) Pettit, G. R.; Grealish, M. P.; Jung, M. K.; Hamel, E.; Pettit, R. K.; Chapuis, J.-C.; Schmidt, J. M. J. Med. Chem. 2002, 45, 2534;
13. (b) Roberti, M.; Pizzirani, D.; Simoni, D.; Rondanin, R.; Baruchello, R.; Bonora, C.; Buscemi, F.; Grimaudo, S.; Tolomeo, M. J. Med. Chem. 2003, 46, 3546;
14. (c) Orsini, F.; Pelizzoni, F.; Bellini, B.; Miglierini, G. Carbohydr. Res. 1997, 301, 95.
15. (a) Ferré-Filmon, K.; Delaude, L.; Demonceau, A.; Noels, A. F. Coord. Chem. Rev. 2004, 248, 2323;
16. (b) Moro, A. V.; Cardoso, F. S. P.; Correia, C. R. D. Tetrahedron Lett. 2008, 49, 5668;
17. (c) Moran, B. W.; Anderson, F. P.; Devery, A.; Cloonan, S.; Butler, W. E.; Varughese, S.; Draper, S. M.; Kenny, P. T. M. Bioorg. Med. Chem. 2009, 17, 4510.
18. In comparison Perkin's method involves a step of decarboxylation at 230°C in quinoline as solvent, see: Ponzoni, C.; Beneventi, E.; Cramarossa, M. R.; Raimondi, S.; Trevisi, G.; Pagnoni, U. M.; Riva, S.; Forti, L. Adv. Synth. Catal. 2007, 349, 1497.
19. This method of cleavage may afford side-products, which hampers isolation of polyphenols in good yield, see: Kendall, P. M.; Johnson, J. V.; Cook, C. E. J. Org. Chem. 1979, 44, 1421.
20. Reimann, E. Liebigs Ann. Chem. 1971, 750, 109.
21. Moreno-Manas, M.; Pleixats, R. An. Quim., Ser. C. 1985, 81, 157.
22. Ruan, B.-F.; Huang, X.-F.; Ding, H.; Xu, C.; Ge, H.-M.; Zhu, H.-L.; Tan, R.-X. Chem. Biodiversity 2006, 3, 975.
23. Biasutto, L.; Mattarei, A.; Marotta, E.; Bradaschia, A.; Sassi, N.; Garbisa, S.; Zoratti, M.; Paradisi, C. Bioorg. Med. Chem. Lett. 2008, 18, 5594.
24. Jiang, Y. L. Bioorg. Med. Chem. 2008, 16, 6406.
25. Poirot, M.; de Medina, P.; Delarue, F.; Perie, J.-J.; Klaebe, A.; Faye, J.-C. Bioorg. Med. Chem. 2000, 8, 2007.
26. Boeva, R.; Markov, K.; Kotov, S. J. Catal. 1985, 62, 231.
27. Bicu, I.; Mustata, F. J. Appl. Polym. Sci. 2002, 83, 802.
28. Heilmann, S. M.; Drtina, G. J.; Janulis, E. P.; Krepski, L. R.; Rasmussen, J. K.; Babirad, S. A.; Moren, D. M.; Bonham, D. S.; Pathre, S. V.; Greening, G. W. J. Fluorine Chem. 1992, 59, 387.
29. (a) Sinhabadu, A. K.; Kawase, M.; Borchardt, R. T. Tetrahedron Lett. 1987, 28, 4139;
30. (b) Saunders, D. G. Synthesis 1988, 377.
31. Guiso, M.; Marra, C.; Farina, A. Tetrahedron Lett. 2002, 43, 597.
32. Learmonth, D. A. Synth. Commun. 2004, 34, 1565.
33. Botella, L.; Najera, C. Tetrahedron 2004, 60, 5563.
34. Andrus, M. B.; Liu, J. Tetrahedron Lett. 2006, 47, 5811.
35. Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Donnadieu, B. Organometallics 2003, 22, 4490.
36. Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M. Tetrahedron 2005, 61, 9759 This ferrocenyl ligand is available fromSTREM (catalog 2012).
37. (a) Saleh, S.; Picquet, M.; Meunier, P.; Hierso, J.-C. Tetrahedron 2009, 65, 7146;
38. (b) Beaupérin, M.; Job, A.; Cattey, H.; Royer, S.; Meunier, P.; Hierso, J.-C. Organometallics 2010, 29, 2815.
39. Bulgarevich, S. B.; Bren, D. V.; Movshovic, D. Y.; Finocchiaro, P.; Failla, S. J. Mol. Struct. 1994, 317, 147.
40. Wang, R.; Lowe, A. B. J. Polym. Sci. 2007, 45, 2468.
41. Bachelor, F. W.; Loman, A. A.; Snowdon, L. R. Can. J. Chem. 1970, 48, 1554.