Chain extension of amino acid skeletons: Preparation of ketomethylene isosteres

Tetrahedron

Volumn 59, Issue 9, 2003, Pages 1521-1527

  Theberge, Cory R ^a   Zercher, Charles K ^a  

^a Univ of New Hampshire   (United States)

Author keywords

Carbenoid; Chain extension; Isostere; Peptide mimic; Zinc

Indexed keywords

AMINO ACID DERIVATIVE; ESTER DERIVATIVE; ZINC;

ARTICLE; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SOLUBILITY;

EID: 0037463516     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00052-8     Document Type: Article

References (20)

1. (a) Dondoni A., Perrone D. Tetrahedron Lett. 33:1992;7259-7262.
2. (b) Young S.D., Payne L.S., Thompson W.J., Gaffin N., Lyle T.A., Brichter S.F., Graham S.L., Schulz T.H., Deana A.A., Darke P.L., Zugay J., Schlerf W.A., Quintero J.C., Emini E.A., Anderson P.S., Huff J.R. J. Med. Chem. 35:1992;1702-1709.
3. (c) Thompson W.J., Fitzgerald P.M.D., Holloway M.K., Emini E.A., Darke P.L., McKeever B.M., Schleif W.A., Quintero J.C., Zugay J.A., Tucker T.J., Schwering J.E., Homnick C.F., Nunberg J., Springer J.P., Huff J.R. J. Med. Chem. 35:1992;1685-1701.
4. (d) Askin D., Wallace M.A., Vacca J.P., Reamer R.A., Volante R.P., Shinkai I. J. Org. Chem. 57:1992;2771-2773.
5. (a) Brogan J.B., Zercher C.K. J. Org. Chem. 62:1997;6444-6446.
6. (b) Verbicky C.A., Zercher C.K. J. Org. Chem. 65:2000;5615-5622.
7. (c) Hilgenkamp R., Zercher C.K. Tetrahedron. 57:2001;8793-8800.
8. Charette A.B., Juteau H., Lebel H., Molinaro C. J. Am. Chem. Soc. 120:1998;11943-11952.
9. (a) Bergmann M., Zervas L. Chem. Ber. 65:1932;1192-1201
10. (b) Wuensch E., Graf W., Keller O., Keller W., Wersin G. Synthesis. 1986;958-960.
11. (c) Allainmat M., L'Haridon P., Toupet L., Plusquellec D. Synthesis. 1990;27-32.
12. (d) Kruse C.H., Holden K.G. J. Org. Chem. 50:1985;2792-2794.
13. (a) Tarbell D.S., Yamamoto Y., Pope B.M. Proc. Natl Acad. Sci. USA. 69:1972;730-732
14. (b) Schnabel E. Liebigs Ann. Chem. 702:1967;188-196.
15. Carpino L.A., Han G.Y. J. Org. Chem. 37:1972;3404-3409.
16. Brooks D.W., Lu L.D.-D., Masamune S. Angew. Chem., Int. Ed. Engl. 18:1979;72-73.
17. (a) Mansour T.S. Synth. Commun. 19:1989;659-665.
18. (b) Mansour T.S., Evans C.A. Synth. Commun. 20:1990;773-781.
19. (a) Lai S.-J., Zercher C.K., Jasinski J.P., Reid S.N., Staples R.J. Org. Lett. 3:2001;4169-4171.
20. (b) Ronsheim M.D., Hilgenkamp R., Zercher C.K. Org. Synth. 79:2002;146-153.