Asymmetric synthesis of a conformationally constrained N-phosphonoalkyl dipeptide

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 19, 1997, Pages 2477-2480

  Wang, Qian ^a   Pfeiffer, Bruno ^b   Tucker, Gordon C ^c   Royer, Jacques ^a   Husson, Henri Philippe ^a  

^a CNRS   (France)

^b ADIR   (France)

^c INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COLLAGENASE INHIBITOR; DIPEPTIDE; PHOSPHONOALKYL DIPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030823182     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10001-4     Document Type: Article

References (13)

1. Henderson, B.; Docherty, A. J. P.; Beeley, N. R. A. Drugs Future 1990, 15, 495-508.
2. Bird, J.; De Mello, R. C.; Harper, G. P.; Hunter, D. J.; Karran, E. H.; Markwell, R. E.; Miles-Williams, A. J.; Rahman, S. S.; Ward, R. W. J. Med. Chem. 1994, 37, 158-169.
3. a) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P J. Am. Chem. Soc. 1983, 105, 7754-7755.
4. b) Bonin, M.; Grierson, D. S.; Royer, J.; Husson, H.-P. Org. Synth. 1992, 70, 54-59.
5. c) Royer, J.; Husson, H.-P. in Advances in the Use of Synthons in Organic Chemistry, Dondonni, A., Ed., JAI Press, London 1995, Vol. 2, p 1-68.
6. a) Maury, C.; Wang, Q.; Gharbaoui, T.; Chiadmi, M.; Tomas, A.; Royer, J.; Husson, H.-P. Tetrahedron, 1997, 53, 3627-3636.
7. b) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687-3693.
8. Berrien, J.-F.; Royer, J.; Husson, H.-P. J. Org. Chem. 1994, 59, 3769-3774.
9. Allylic ester was chosen in order to give the possibility of a selective deprotection of the carboxylic acid moiety on further step.
10. Genêt, J.P.; Blart, E.; Savignac, M.; Lemeune, S.; Lemaire-Audoire, S.; Bernard, J.M. Synlett 1993, 683.
11. C-P=140Hz), 29.2, 27.2, 26.7, 24.9, 19.6 (d, J=7Hz).
12. from Dr. Gillian Murphy, Strangeways Laboratories, Cambridge, UK.
13. Bickett, D.M.; Green, M.D.; Berman, J.; Dezube, M.; Howe, A.S.; Brown, P.J.; Roth, J.T.; Mc Geehan, G.M. Anal. Biochem. 1993, 212, 58-64.