The first practical asymmetric synthesis of R and S-warfarin

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8321-8324

  Robinson, Andrea ^a   Li, Hui Yin ^a   Feaster, John ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

WARFARIN;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0030580374     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01796-0     Document Type: Article

References (33)

1. 1. (a) Crossley, R. Tetrahedron 1992, 48, 8155.
2. (b) Dicicco, R. L. In Chiral' 93 USA, Reston, Virginia, 1993, p 5-7.
3. (c) Richards, A. In ibid Reston, Virginia, 1993, p 75.
4. (d) Brown, C. Chirality in Drug Design and Synthesis; Academic Press Inc.: San Diego, 1990.
5. (e) Ariens, E. J.; Soudijin, W.; Timmermans, P. B. M. W. M. Stereochemistry and Biological Activity of Drugs; Blackwell Scientific Publications: Osney Mead, Oxford, 1983.
6. 2. Recent reviews: (a) Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers, Inc.: New York, 1993.
7. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
8. (c) Ager, D. J.; East, M. B. Asymmetric Synthetic Methodology; CRC Press, Inc.: Boca Raton, Florida, 1995.
9. 3. Enantioselective reduction of α,β-unsaturated carboxamides has been reported: Matt, P. Pfaltz, A. Tetrahedron: Asymmetry 1991, 2, 691. Asymmetric hydrogenation of α,β-unsaturated aldehydes with moderate enantioselectivity has been reported: Dang, T.-P.; Aviron-Violet P.; Colleuille et Jean Y. J. Mol. Cat. 1982, 16, 51.
10. 3. Enantioselective reduction of α,β-unsaturated carboxamides has been reported: Matt, P. Pfaltz, A. Tetrahedron: Asymmetry 1991, 2, 691. Asymmetric hydrogenation of α,β-unsaturated aldehydes with moderate enantioselectivity has been reported: Dang, T.-P.; Aviron-Violet P.; Colleuille et Jean Y. J. Mol. Cat. 1982, 16, 51.
11. 4. (a) Reilly, R. A.; Aggeler, P. M. Pharmacol. Rev. 1970, 22, 35.
12. (b) O'Reilly, R. A. Pharmacology 1972, 8, 181-90.
13. (c) Ikawa, M.; Stahmann, M. A.; Link, K. P. J. Am. Chem. Soc. 1944, 66, 902.
14. 5. Trager, W. F. Probl. Wonders Chiral Mol 1990.
15. 6. (a) Kaminsky, L. S.; de Morais, S. M. F.; Faletto, M. B.; Dunbar, D. A.; Goldstein, J. A. Molecular Pharmacology 1992, 43, 234.
16. (b) Kunze, K. L.; Eddy, A. C.; Gibaldi, M.; Trager, W. F. Chirality 1991, 3, 24.
17. (c)Lawrence, R. F.; Rettie, A. E.; Eddy, A. C.; Trager, W. F. Chirality 1990, 2, 96.
18. 7. West, B. D.; Preis, S.; Schroeder, C. H.; Link, K. P. J. Am. Chem. Soc. 1961, 83, 2676.
19. 8. (a) Cook, C. E.; Ballentine, N. H.; Seltxman, T. B.; Tallent, C. R. J. Pharmacol. Exp. Ther. 1979, 210, 391.
20. (b) Soini, H.; Stefansson, M.; Riekkola, M.-L.; Novotny, M. V. Anal. Chem. 1994, 66, 3477.
21. (c) Armstrong, D. W.; Zhou, E. Y.; Chen, S.; Le, K.; Tang, Y. Anal. Chem. 1994, 66, 4278.
22. (d) Bargmann-Leyder, N.; Tambute, A.; Begos, A.; Caude, M. Chromatographia 1993, 37, 433.
23. 9. Fasco, M. J.; Dymerski, P. P.; Wos, J. D.; Kaminsky, L. S. J. Med. Chem. 1978, 21, 1054.
24. 10. Toussaint, O.; Capdevielle, P.; Maumy, M. Tetrahedron. Lett. 1984, 3819.
25. 11. Chan, A. S. C.; Pluth, J. J.; Halpern, J. J. Am. Chem. Soc. 1980, 102, 5952 and references cited therein.
26. 12. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
27. 13. (a) Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3174.
28. (b) Ohta, T.; Takaya, T.; Noyori, R. Tetrahedron Lett 1990, 31, 7189.
29. (c) Zhang, X.; Uemura, T.; Sayo, N.; Kumobayashi, H.; Takaya, H. Synlett 1994, 501.
30. 14. Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995, 60, 357.
31. 15. Stoll, W.; Litvan, F. U.S. pat. , 2,648,682 (CA 49:2533g).
32. 16. Jindal, M. N.; Shah, D. S. Arzneimittal-Forsch. 1966, 16, 878.
33. 17. Wanntorp, H. Acta Pharmacol. Toxicol. 1959, 16, 123.