Synthesis of Conformationally Restricted Amino Acids and Peptides Employing Olefin Metathesis

Journal of the American Chemical Society

Volumn 117, Issue 21, 1995, Pages 5855-5856

  Miller, Scott J ^a   Grubbs, Robert H ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PEPTIDE SYNTHESIS; STEREOCHEMISTRY;

EID: 0029033474     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00126a027     Document Type: Article

References (23)

1. For an overview of the field, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
2. Tetrahedron Symposia-in-Print No. 50 1993, 49 (17), 3433.
3. Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
4. Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249.
5. Toniolo, C. Int. J. Pept. Protein Res. 1990, 35, 287.
6. Previous reports on RCM from this laboratory: (a) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 5426.
7. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
8. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800.
9. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
10. Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029.
11. Kim, S. H.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801.
12. Miller, S. J.; Kim, S. H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108.
13. For recent applications of RCM to natural product synthesis: (h) Martin, S. F.; Liao, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691.
14. Borer, B. C.; Deerenberg, S.; Bieraugel. H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191.
15. Martin, S. F.; Wagman, A. S. Tetrahedron Lett. 1995, 36, 1169.
16. Houri, A. F.; Xu, Z.; Cogan, D.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. For a review on applications of olefin metathesis in organic synthesis: Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon; New York, 1991; Vol. 5, Chapter 9.3.
17. For the preparation and characterization of catalyst 1: (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974.
18. Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858.
19. Pietzonka, T.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1481.
20. For discussions of β-turns in proteins, see: (a) Rizo, J.; Gierasch, L. M. Annu. Rev. Biochem. 1992, 61, 387.
21. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1. For a review of β-turn mimetics, see ref 1b.
22. Ravi, A.; Balaram, P. Tetrahedron 1984, 40, 2577.
23. The disulfide dihedral angle in 10 has been shown to be 82° with right-handed chirality in the solid state. Ravi, A.; Prasad, B. V.; Balaram, P. J. Am. Chem. Soc. 1983, 105, 105.