A modular rearrangement approach toward medicinally relevant phosphinic structures

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4696-4699

  Rogakos, Vassilis ^a   Georgiadis, Dimitris ^a   Dive, Vincent ^b   Yiotakis, Athanaslos ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b Institute Frederic Joliot   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; CARBON; PHOSPHINIC ACID DERIVATIVE; PHOSPHORUS;

ARTICLE; CHEMISTRY; MEDICINE;

ACRYLATES; CARBON; MEDICINE; PHOSPHINIC ACIDS; PHOSPHORUS;

EID: 70349900381     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902004p     Document Type: Article

References (39)

1. For reviews, see: (a) Enders, D.; Saint-Dizier, A.; Lannou, M.-L; Lenzen, A. Eur. J. Org. Chem. 2006, 29.
2. (b) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
3. (c) Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035.
4. For reviews on phosphorous-containing peptidomimetics, see: (a) Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity; Kukhar, V. P., Hudson, H. R., Eds.; John Wiley & Sons: Chichester, 2000.
5. (b) Collinsová, M.; Jirácek, J. Curr. Med. Chem. 2000, 7, 629.
6. (c) Yiotakis, A.; Georgiadis, D.; Matziari, M.; Makaritis, A.; Dive, V. Curr. Org. Chem. 2004, 8,1135.
7. (d) Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899.
8. For selected examples, see: (a) Dive, V.; Cotton, J.; Yiotakis, A.; Michaud, A.; Vassiliou, S.; Jiráček, J.; Vazeux, G.; Chauvet, M.-T.; Cuniasse, P.; Corvol, P. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4330.
9. (b) Georgiadis, D.; Beau, F.; Czarny, B.; Cotton, J.; Yiotakis, A.; Dive, V. Circ. Res. 2003, 93, 148.
10. (c) Devel, L.; Rogakos, V.; David, A.; Makaritis, A.; Beau, F.; Cuniasse, P.; Yiotakis, A.; Dive, V. J. Biol. Chem. 2006, 281, 11152.
11. (d) Chen, H.; Noble, F.; Coric, P.; Fournie-Zaluski, M.-C.; Roques, B. P. Proc Natl. Acad. Sci. U.S.A. 1998, 95, 12028.
12. (e) LauerFields, J.; Brew, K.; Whitehead, J. K.; Li, S.; Hammer, R. P.; Fields, G. B. J. Am. Chem. Soc. 2007, 129, 10408.
13. (f) Liu, X.; Xu, X. E.; Tian, X.; Mazur, A.; Ebetino, F. H. Organomet. Chem. 2002, 646, 212.
14. For selected recent examples, see: (a) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836.
15. (b) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
16. (c) Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
17. (d) Cho, C. W.; Krische, M. J. Angew. Chem., Int. Ed. 2004, 43, 6689.
18. (e) Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260.
19. (f) Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1426.
20. (g) Cowen, B. J.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 10988.
21. (h) Fang, Y.-Q.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 5660.
22. For a phosphonium zwitterion isolated during a phosphine-catalyzed Morita-Baylis-Hillman reaction, see: (a) Zhu, X.-F.; Henry, C. E.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 6722.
23. For a tandem P - C/C - C bondforming reaction involving phosphides, see: (b) Hayashi, M.; Matsuura, Y.; Watanabe, Y. Tetrahedron Lett. 2005, 46, 5135.
24. Hanamoto, T.; Baba, Y.; Inanaga, J. J. Org. Chem. 1993, 58, 299.
25. For Ireland-Claisen rearrangements triggered by conjugate additions, see: (a) Aoki, Y.; Kuwajima, I. Tetrahedron Lett. 1990, 31, 7457.
26. (b) Yamazaki, T.; Shinohara, N.; Kitazume, T.; Sato, S. J. Org. Chem. 1995, 60, 8140.
27. (c) Eriksson, M.; Hjelmencrantz, A.; Nilsson, M.; Olsson, T. Tetrahedron 1995, 51, 12631.
28. (d) Takai, K.; Ueda, T.; Kaihara, H.; Sunami, Y.; Moriwake, T. J. Org. Chem. 1996, 61, 8728.
29. (e) Bausch, C. C.; Johnson, J. S. J. Org. Chem. 2008, 73, 1575.
30. FOT a relevant reaction with oxasilacyclopentenes, see: (f) Calad, S. A.; Woeprel, K. A. J. Am. Chem. Sag. 2005, 127, 2046.
31. Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1977, 100, 3467.
32. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
33. For reviews, see: (a) Toniolo, C. Biopolymers 1989, 28, 247.
34. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039.
35. (c) Gante, J. Angew. Chem., Int. Ed. 1994, 33, 1699.
36. (d) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
37. For the only literature report of a relevant phosphinopeptidic structure, see: McKittrick, B. A.; Stamford, A. W.; Weng, X.; Ma, K.; Chackalamannil, S.; Czarniecki, M.; eleven, R. M.; Fawzi, A. B. Bioorg. Med. Chem. Lett. 1996, 6, 1629.
38. Smith, A. B.; Ducry, L.; Corbett, R. M.; Hirschmann, R. Org. Lett. 2000, 2, 3887-3890.
39. Gomis-Rüth, F. X. Crit. Rev. Biochem. Mol. Biol. 2008, 43, 319.