Shortcut to Fmoc-protected phosphinic pseudodipeptidic blocks

Organic Letters

Volumn 7, Issue 18, 2005, Pages 4049-4052

  Matziari, Magdalini ^a   Yiotakis, Athanasios ^a  

^a UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORENE DERIVATIVE; PEPTIDE; PHOSPHINIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; FLUORENES; MOLECULAR STRUCTURE; PEPTIDES; PHOSPHINIC ACIDS;

EID: 24944562424     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051622y     Document Type: Article

References (44)

1. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
2. Birum, G. H. J. Org. Chem. 1974, 39, 209.
3. (a) Oleksyszyn, J.; Tyka, R.; Mastalerz, P. Synthesis 1978, 479.
4. (b) Oleksyszyn, J.; Subotkowska, L.; Mastalerz, P. Synthesis 1979, 985.
5. (c) Oleksyszyn, J.; Gruszecka, E. Tetrahedron Lett. 1981, 22, 3537.
6. (d) Oleksyszyn, J. J. Prakt. Chem. 1987, 329, 19.
7. Chen, S.; Coward, J. K. J. Org. Chem. 1998, 63, 502.
8. (a) Georgiadis, D.; Beau, F.; Czarny, B.; Cotton, J.; Yiotakis, A.; Dive, V. Circ. Res. 2003, 93, 148.
9. (b) Acharya, K. R.; Sturrock, E. D.; Riordan, J. F.; Ehlers, M. R. W. Nat. Rev. Drug Discov. 2003, 2, 891.
10. (a) Matziari, M.; Beau, F.; Cuniasse, P.; Dive, V.; Yiotakis, A. J. Med. Chem. 2004, 47, 325.
11. (b) Reiter, L. A.; Mitchell, P. G.; Martinelli, G. J.; Lopresti-Morrow, L. L.; Yocum, S. A.; Eskra, J. D. Biorg. Med. Chem. Lett. 2003, 13, 2331.
12. (c) Schiodt, C. B.; Buchardt, J.; Terp, G. E.; Christensen, U.; Brink, M.; Berger Larsen, Y.; Meldal, M.; Foged, N. T. Curr. Med. Chem. 2001, 8, 967.
13. Georgiadis, D.; Vazeux, G.; Llorens-Cortes, C.; Yiotakis, A.; Dive, V. Biochemistry 2000, 39, 1152.
14. Grembecka, J.; Mucha, A.; Cierpicki, T.; Kafarski, P. J. Med. Chem. 2003, 46, 2641.
15. (a) Makaritis, A.; Georgiadis, D.; Dive, V.; Yiotakis, A. Chem. Eur. J. 2003, 9, 2079.
16. (b) Buchardt, J.; Schiodt, C. B.; Krog-Jensen, C.; Delaisse, J. M.; Foged, N. T.; Meldal, M. J. Comb. Chem. 2000, 6, 624.
17. (a) Dive, V.; Cotton, J.; Yiotakis, A.; Michaud, A.; Vassiliou, S.; Jiracek J.; Vazeaux, G.; Chauvet, M.-T.; Cuniasse, P.; Corvol, P. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4330.
18. (b) Jiracek, J.; Yiotakis, A.; Vincent, B.; Checler, F.; Dive, V. J. Biol. Chem. 1996, 271, 19606.
19. (a) Nomenclature based on that used in: Schechter, I.; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, 157.
20. (b) Gall, A.-L.; Ruff, M.; Kannan, R.; Cuniasse, P.; Yiotakis, A.; Dive, V.; Rio, M.-C.; Basset, P.; Moras, D. J. Mol. Biol. 2001, 307, 577.
21. (c) Grams, F.; Dive, V.; Yiotakis, A.; Yiallouros, I.; Vassiliou, S.; Zwilling, R.; Bode W.; Stöcker, W. Nature Struct. Biol. 1996, 3, 671.
22. (a) Yiotakis, A.; Georgiadis, D.; Matziari, M.; Makaritis, A.; Dive, V. Curr. Org. Chem. 2004, 8, 1135.
23. (b) Dive, V.; Georgiadis, D.; Matziari, M.; Makaritis, A.; Beau, F.; Cuniasse, P.; Yiotakis, A. Cell. Mol. Life Sci. 2004, 61, 2010.
24. (a) Yiotakis, A.; Vassiliou, S.; Jiracek, J.; Dive, V. J. Org. Chem. 1996, 61, 6601.
25. (b) Campagne, J.-M.; Coste, J.; Guillou, L.; Heitz, A.; Jouin, P. Tetrahedron Lett. 1993, 34, 4181.
26. (c) Georgiadis, D.; Matziari, M.; Yiotakis, A. Tetrahedron 2001, 57, 3471.
27. (d) Miller, D. J.; Hammond, S. M.; Anderluzzi, D.; Bugg. T. D. H. J. Chem. Soc., Perkin Trans. 1 1998, 131.
28. (a) Matziari, M.; Georgiadis, D.; Dive, V.; Yiotakis, A. Org. Lett. 2001, 3, 659.
29. (b) Georgiadis, D.; Matziari, M.; Vassiliou, S.; Dive, V.; Yiotakis, A. Tetrahedron 1999, 55, 14635.
30. (c) Kende, A. S.; Dong, H.-Q.; Liu, X.; Ebetino, F. H. Tetrahedron Lett. 2002, 43, 4973.
31. Baylis, E. K.; Campbell, C. D.; Dingwall, J. D. J. Chem. Soc., Perkin Trans. 1 1984, 2845.
32. (a) Boyd, E. A.; Regan, A. C.; James, K. Tetrahedron Lett. 1992, 33, 813.
33. (b) Boyd, E. A.; Corless, M.; James, K.; Regan, A. C. Tetrahedron Lett. 1990, 31, 2933.
34. 2 is commercially available from Fluka or can be synthesized as described in: Carpino, L. A.; Mansour, E. M. E.; Cheng, C. H.; Williams, J. R.; MacDonald, R.; Knapczyk, J.; Carman, M.; Lopusinski, A. J. Org. Chem. 1983, 48, 661.
35. Chen, S.; Coward, J. K. Tetrahedron Lett. 1996, 37, 4335.
36. Taylor, W. G. J. Org. Chem. 1981, 46, 4290.
37. Simoneau, B.; Savard, J.; Brassard, P. J. Org. Chem. 1985, 50, 5434.
38. (a) Gannet, P. M.; Nagel, D. L.; Reilly, P. J.; Lawson, T.; Sharpe, J.; Toth, B. J. Org. Chem. 1988, 53, 1064.
39. (b) Gutman, A. L.; Boltanski, A. J. Chem. Soc., Perkin Trans. 1 1989, 47.
40. Pham, T.; Lubell, W. D. J. Org. Chem. 1994, 59, 3676.
41. Ku, T. W.; McCarthy, M. E.; Weichman, B. M.; Gleason, J. G. J. Med. Chem. 1985, 28, 1847.
42. Hershberg, E. B.; Cason, J. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 627.
43. Su, Q.; Wood, J. L. Synth. Commun. 2000, 30, 3383.
44. Buchardt, J.; Ferreras, M.; Krog-Jensen, C.; Delaissé, J. M.; Foged, N. T.; Meldal, M. Chem. Eur. J. 1999, 5, 2877.