Using cross-metathesis to couple L-phenylalanine to a macrocyclic lactam

Journal of Organic Chemistry

Volumn 71, Issue 6, 2006, Pages 2272-2276

  Enholm, Eric ^a   Low, Tammy ^a  

^a University of Florida   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-METATHESIS; L-PHENYLALANINE; MACROCYCLIC LACTAM;

CATALYSTS; OLEFINS; RUTHENIUM;

AMINO ACIDS;

ALKENE; AMINO ACID; LACTAM DERIVATIVE; MACROCYCLIC COMPOUND; PHENYLALANINE; RUTHENIUM;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; CRYSTALLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS;

CATALYSIS; LACTAMS, MACROCYCLIC; MOLECULAR STRUCTURE; PHENYLALANINE; RUTHENIUM; STEREOISOMERISM;

EID: 33645030933     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052415e     Document Type: Article

References (21)

1. Hanessian, S.; McNaughton-Smith, G.: Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-854.
2. Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-48.
3. Eguchi, M.; Shen, R. Y. W.; Shea, J. P.; Lee, M. S.; Kahn, M. J. Med. Chem. 2002, 45, 1395-98.
4. Le, G. T.; Abbenante, G.; Becker, B.; Grathwohl, M.; Halliday, J.; Tometzki, G.; Zuegg, J.; Meutermans, W. Drug Discovery Today 2003, 8, 701-9.
5. Hu, X,; Nguyen, K. T.; Jiang, V. C.; Lofland, D.; Moser, H. E.; Pei, D. J. Med. Chem. 2004, 47, 4941-9.
6. (a) Chatterjee, A. K.; Choi, T. L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-70.
7. (b) Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035-37.
8. (c) Grubbs, R. H. Tetrahedron 2004, 60, 7117-40.
9. (d) Salim, S. S.; Bellingham, R. K.; Brown, R. C. D. Eur. J. Org. Chem. 2004, 800-6.
10. (a) Yun, J.; Marinez, E. R.; Grubbs, R. H. Organometallics 2004, 23, 4172-3.
11. (b) Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125 (33), 10103-9.
12. (c) Trnka, T. M.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T. E.; Scholl, M.; Choi, T. L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125 (9), 2546-58.
13. (a) Fisher, R. A.; Grubbs, R. H. Makromol. Chem., Macromol. Symp. 1992, 63, 271-77.
14. (b) Smith, A. B.; Adams, C. M.; Kozmin, S. A., J. Am. Chem. Soc. 2001, 123, 990-91.
15. Gibson, H. W.; Nagvekar, D. S.; Delaviz Y. Can. J. Chem. 1998, 76, 1429-36.
16. Ivin, K. J. J. Mol. Catal. A: Chem. 1998, 133, 1-16.
17. Sachinvala, N. D.; Winsor, D. L.; Hamed, O. A. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1889-02.
18. Takeda, K.; Akiyama, A.; Nakamura, H.; Takizawa, S.; Mizuno, Y.; Takayanagi, H.; Harigaya, Y. Synthesis 1994, 10, 1063-66.
19. Hue, I.; Nguyen, R. Comb. Chem. High Throughput Screening 2001, 4, 109-30.
20. Casadei, M. A.; Cesa, S.; Inesi, A. Tetrahedron 1995, 51, 5891-00.
21. The views in this article are those of the authors and do not reflect the official policy or position of the United States Air Force, Department of Defense, or the U.S. Government.