A simple route to 4-substituted-3,4-didehydroprolines, mechanistic probes for the inhibition of prolyl-4-hydroxylase

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5399-5402

  Koskinen, Ari M P ^a   Schwerdtfeger, Jörg ^a   Edmonds, Michael ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

PROCOLLAGEN PROLINE 2 OXOGLUTARATE 4 DIOXYGENASE; PROLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; TECHNIQUE;

EID: 0030745172     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01182-9     Document Type: Article

References (34)

1. For leading references, cf. (a) Barlow, D.J.; Thornton, J.M. J. Mol. Biol. 1988, 201, 601.
2. (b) Koskinen, A.M.P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859.
3. (c) Ibrahim, H.H.; Lubell, W.D. J. Org. Chem. 1993, 58, 6438.
4. 3,4-dehydroproline (a) Dormoy, J.-R. Synthesis 1982, 753.
5. (b) Rüeger, H.; Benn, M.H. Can. J. Chem. 1982, 60, 2918.
6. 4-alkylideneproline (a) Moody, C.M.; Young, D.W. Tetrahedron Lett. 1993, 34, 4667-4770.
7. (b) Panday, S.K.; Griffart-Brunet, D.; Langlois, N. Tetrahedron Lett. 1994, 35, 6673.
8. (c) Bethell, M.; Kenner, G.W. J. Chem. Soc. 1965, 3850.
9. (d) Herdewijn, P.; Claes, P.J.; Vanderhaeghe, H. Can. J. Chem. 1982, 60, 2903.
10. (e) Patchett, A.A.; Witkop, B. J. Am. Chem. Soc. 1957, 79, 185.
11. (f) Dormoy, J.-R.; Castro, B. Synthesis 1986, 81.
12. (g) Adlington, R.M.; Mantell, S.J. Tetrahedron 1992, 48, 6529.
13. (h) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060.
14. Horikawa, M.; Shirahama, H. Synlett 1996, 95.
15. Kivirikko, K.I.; Myllylä, R.; Pihlajaniemi, T. in: Post translational modifications of proteins, J.J. Harding, M.J.C. Crabbe (eds.), CRS Press, 1992, Chapter 1, and references cited therein,
16. (b) Kivirikko, K.I.; Myllylä, R; Pihlajaniemi, T. FASEB J. 1989, 3, 1609.
17. Dowell, R.I.; Hadley, E.M. J. Med. Chem. 1992, 35, 800.
18. Remuzon, P. Tetrahedron 1996, 52, 13803.
19. (a) Christie, B.D.; Rapoport, H. J. Org. Chem. 1985, 50, 1239.
20. (b) Gmeiner, P.; Feldman, P.L.; ChuMoyer, M.Y.; Rapoport, H. J. Org. Chem. 1990, 55, 3068.
21. (c) Lubell, W.D.; Jamison, T.F.; Rapoport, H. J. Org. Chem. 1990, 55, 3511.
22. (d) Lubell, W.D.; Rapoport, H. J. Org. Chem. 1989, 54, 3824.
23. (e) Lubell, W.D.; Rapoport, H. J. Am. Chem. Soc. 1987, 709, 236.
24. (a) Gill, P.; Lubell, W.D. J. Org. Chem. 1995, 60, 2658.
25. (b) Blanco, M.J.; Sardina, F.J. Tetrahedron Lett. 1994, 35, 8493-8496.
26. All new compounds gave satisfactory spectral and analytical data (HRMS or elemental analysis).
27. Corey, E.J.; Suggs, J.W. Tetrahedron Lett. 1975, 2647.
28. Mancuso, A.J.; Huang, S.-L.; Swern, D., J. Org. Chem. 1978, 43, 2480.
29. 2(1 atm) and Boc anhydride.
30. Comins, D.L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
31. (a) Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1985, 108, 3033-3040.
32. (b) Renaldo, A.F.; Labadie, J.W.; Stille J.K. Org. Synth. 1988, 68, 87.
33. (a) Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1985, 1109.
34. (b) Cacchi, S.; Lupi, A. Tetrahedron Lett. 1992, 33, 3939.