A Highly Stereoselective Michael Addition to an α,β-Unsaturated Ester as the Crucial Step in the Synthesis of a Novel β-Amino Acid-Containing Fibrinogen Receptor Antagonist

Journal of Organic Chemistry

Volumn 58, Issue 27, 1993, Pages 7948-7951

  Rico, Joseph G ^a   Lindmark, Richard J ^a   Rogers, Thomas E ^a   Bovy, Philippe R ^a  

^a MONSANTO COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITHROMBOCYTIC AGENT; BETA [[4 [(4 AMIDINOPHENYL)AMINO] 1,4 DIOXOBUTYL]AMINO] 3 PYRIDINEPROPIONIC ACID; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0027729388     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00079a054     Document Type: Note

References (21)

1. For reviews: Barrett, G. C., Ed. Chemistry and Biochemistry of the Amino Acids; Chapman and Hall: London New York, 1985; p 25.
2. Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855–78.
3. For some additional examples, see: Konopelski, J.; Chu, K. S.; Negrete, G. R. J. Org. Chem. 1991, 56, 1355–1357.
4. Kato, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1988, 29, 6465–6.
5. Baldwin, J. E.; Adlington, R. M.; O'Neil, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc. Chem. Commun. 1989, 1852. See also ref 7.
6. Tjoeng, F. S.; Fok, K. F.; Zupec, M. E.; Garland, R. B.; Miyano, M.; Panzer-Knodle, S. G.; King, L. W.; Nicholson, N. S.; Taite, B. B.; Feigen, L. P.; Adams, S. P. In Peptides: Chemistry, Structure and Biology (Proceedings of the 12th American Peptide Symposium; Smith, J. A., Rivier, J. E., Eds.; Escom: Leiden, The Netherlands, 1992; p 752.
7. Bovy, P. R.; Garland, R. B.; Tjoeng, F. S.; Zupec, M. E.; Zablocki, J. A.; Rico, J. G.; Rogers, T. E.; Lindmark, R. J.; Panzer-Knodle, S. G.; Nicholson, N. S.; Taite, B. B.; Miyano, M.; Feigen, L. P.; Adams, S. P. J. Cell. Biochem. Suppl. C 1993, L 308.
8. Bovy, P. R.; Rico, J. G.; Rogers, T. E.; Tjoeng, S. F.; Zablocki, J. PCT Int. Appl. WO 93/07867, 1993.
9. Secor, H. V.; Edwards, W. B. J. Org. Chem. 1979, 44, 3136–3140.
10. Bellasoued, M.; Arous-Chtara, R.; Gaudemar, M. J. Organometal. Chem. 1982, 231, 185–89.
11. Furukawa, M.; Okarawa, T.; Noguchi, Y.; Trawaki, Y. Chem. Pharm. Bull. 1978, 26, 260–63.
12. Madigan, D. L.; Walters, D. E.; Culberson, J. C.; Dubois, G. E.; Carter, J. S.; Nagarajan, S.; Klix, R. C.; Ager, D. J.; Klade, C. A. EP 355819, 1990.
13. Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1991, 2, 183–186.
14. Furukawa, M.; Okarawa, T.; Terawaki, Y. Chem. Pharm. Bull. 1977, 25, 1319–1325.
15. Pearlman, W. M. Tetrahedron Lett. 1967, 1663.
16. Bernotas, R.; Cube, R. C. Synth. Commun. 1990, 20, 1209–12.
17. Adger, B. M.; O'Farrell, C.; Lewis, N. J.; Mitchell, M. B. Synthesis 1987, 53.
18. Khan, S. A.; Sivanandaiah, K. M. Synthesis 1978, 750.
19. Lalonde, M.; Chan, T. H. Synthesis 1985, 817–845.
20. Possible d-orbital participation in the formation of σ-bonds, stabilization of reaction intermediates and transition states, and the formation of internal x-bonds have been proposed, Onan, K. D.; McPhail, A. T.; Yoder, C. H.; Hillard, R. W. J. Chem. Soc. Chem. Commun. 1978, 209.
21. Perozzi, E. F.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 1591.