A practical radical based access to functionalised geminal bisphosphonates

Synlett

Volumn , Issue 3, 2003, Pages 387-389

  Gagosz, Fabien ^a   Zard, Samir Z ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

Bisphosphonates; Radical reactions; Xanthates

Indexed keywords

ALKENE DERIVATIVE; PEROXIDE; PHOSPHONIC ACID DERIVATIVE; RADICAL; XANTHIC ACID DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; ELECTRON; MOLECULAR DYNAMICS; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 0037288240     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37108     Document Type: Article

References (30)

1. (a) Fleisch, H. A New Class of Drugs in Diseases of Bone and Calcium Metabolism. In Handbook of Experimental Pharmacology, Vol. 83; Baker P. F., Springer: Berlin/Heidelberg, 1988, 441-465.
2. (b) Geddes, A. D.; D'Souza, S. M.; Ebetino, F. H.; Ibbotson, K. J. In Bone and Mineral Research; Elsevier Science: New York, 1994.
3. (c) Widler, L.; Jaeggi, K. A.; Glatt, M.; Müller, K.; Bachmann, R.; Bisping, M.; Born, A.-R.; Cortesi, R.; Guiglia, G.; Jeker, H.; Klein, R.; Ramseier, U.; Schmid, J.; Schreiber, G.; Seltenmeyer, Y.; Green, J. R. J. Med. Chem. 2002, 45, 3721.
4. (a) Smith, R.; Russell, R. G. G.; Bishop, M. Lancet 1971, i, 945.
5. (b) O'Doherty, D. P.; Bickerstaff, D. R.; McCloskey, E. V.; Hamdy, N. A. T.; Beneton, M. N. C.; Harris, S.; Mian, M.; Kanis, J. A. J. Bone Miner. Res. 1990, 5, 483.
6. Morton, A. R.; Cantrill, J. A.; Pillai, G. V.; McMahon, A.; Anderson, D. C.; Howell, A. Br. Med. J. 1988, 297, 772.
7. (a) Storm, T.; Thamsborg, G.; Steiniche, T.; Genant, H. K.; Sorensen, O. H. N. Engl. J. Med. 1990, 322, 1265.
8. (b) Reginster, J. Y.; Deroisy, R.; Denis, D.; Collette, J.; Lecart, M. P.; Sarlet, N.; Ethgen, D.; Franchimont, P. Lancet 1989, ii, 1469.
9. (a) Schlachter, S. T.; Galinet, L. A.; Shields, S. K.; Aspar, D. G.; Dunn, C. J.; Staite, N. D.; Nugent, R. A. Bioorg. Med. Chem. Lett. 1998, 8, 1093.
10. (b) Nugent, R. A.; Schlachter, S. T.; Murphy, M.; Dunn, C. J.; Staite, N. D.; Galinet, L. A.; Shields, S. K.; Wu, H.; Aspar, D. G.; Richard, K. A. J. Med. Chem. 1994, 37, 4449.
11. (a) Bijvoet, O. L.; Frijlink, W. B.; Jie, K.; Van der Linden, H.; Meijer, C. J.; Mulder, H.; Van Paassen, H. C.; Reitsma, P. H.; De velde, J.; De Vries, E.; Van der Wey, J. Arthritis Rheum. 1980, 23, 1193.
12. (b) Ralston, S. H.; Willocks, L. J.; Hacking, L.; Pitkeathly, D. A. Calc. Int. 1988, 42, 23.
13. Byers, J. H.; Thissell, J. G.; Thomas, M. A. Tetrahedron Lett. 1995, 36, 6403.
14. (a) Zard, S. Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 672; and references cited.
15. (b) Quiclet-Sire, B.; Zard, S. Z. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 153; and references cited.
16. (c) Quiclet-Sire, B.; Zard, S. Z. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 137; and references cited.
17. For a synthetic study concerning the sulfenylation of tetraalkylmethylene-bisphosphonates, see: Mikolajczyk, M.; Balczewski, P.; Grzejszczak, S. Synthesis 1980, 127.
18. +).
19. 2: C, 34.51; H, 5.79. Found: C, 34.61; H, 5.88.
20. Liard, A.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 1996, 37, 5877.
21. Barbier, F.; Pautrat, F.; Zard, S. Z. Synlett 2002, 811.
22. (a) Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2000, 122, 6496.
23. (b) Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2001, 123, 4717.
24. (a) Kim, S.; Song, H.-J.; Choi, T.-L.; Yoon, J.-Y. Angew. Chem. Int. Ed. 2001, 40, 2524.
25. (b) Bertrand, F.; Le Guyader, F.; Liguori, L.; Ouvry, G.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. C. R. Acad. Sci. 2001, 4, 547.
26. (c) Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem. Int. Ed. 1998, 37, 2864.
27. (d) Bertrand, F.; Quiclet-Sire, B.; Zard, S. Z. Angew. Chem. Int. Ed. 1999, 38, 1943.
28. (e) Liard, A.; Quiclet-Sire, B.; Saicic, R. N.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 1759.
29. (f) Ly, T.-M.; QuicletSire, B.; Sortais, B.; Zard, S. Z. Tetrahedron Lett. 1999, 40, 2533.
30. (g) Kaoudi, T.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem. Int. Ed. 2000, 39, 731.