Progress toward the total synthesis of callipeltin A (I): Asymmetric synthesis of (3S,4R)-3,4-dimethylglutamine

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4157-4160

  Liang, Bo ^a   Carroll, Patrick J ^a   Joullié, Madeleine M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIMETHYLGLUTAMINE; 3,4-DIMETHYLGLUTAMINE; CALLIPELTIN A; CYCLOPEPTIDE; DEPSIPEPTIDE; DRUG DERIVATIVE; GLUTAMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

DEPSIPEPTIDES; GLUTAMINE; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC;

EID: 0034727947     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006679t     Document Type: Article

References (30)

1. Ireland, C. M.; Molinski, T. F.; Roll, D. M.; Zabriskie, T. M.; McKee, T. C.; Swersey, J. C.; Foster, M. P. Natural Product Peptides from Marine Organisms. In Biorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag: Berlin Heidelberg, 1989; pp 1-46.
2. (a) Zampella, A.; Valeria D'Auria, M.; Gomez Paloma, L.; Casapullo, A.; Minale, L.; Debitus, C.; Henin, Y. J. Am. Chem. Soc. 1996, 118, 6202-6209.
3. (b) Valeria D'Auria, M.; Zampella, A.; Gomez Paloma, L.; Minale, L. Tetrahedron 1996, 52, 9589-9596.
4. (a) Yamaguchi, M.; Tsukamoto, M.; Tanaka, S.; Hirao, I. Tetrahedron Lett. 1984, 25, 5661-5664.
5. (b) Blarer, S. J.; Schweizer, W. B.; Seebach, D. Helv. Chim. Acta 1982, 65, 1637-1654.
6. (c) Kawasaki, H.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1985, 25, 3031-3034.
7. (d) Yamaguchi, M.; Hasebe, K.; Tanaka, S.; Minami, T. Tetrahedron Lett. 1986, 27, 959-962.
8. (a) Heathcock, C. H.; Henderson, M. A.; Oare, D. A.; Sanner, M. A. J. Org. Chem. 1985, 50, 3019.
9. (b) Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 132-157.
10. (a) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806 and references therein.
11. (b) Oppolzer, W.; Poli, G. Tetrahedron Lett. 1986, 27, 4717-4720.
12. (a) Evans, D. A.; Britton, T. C. J. Am. Chem. Soc. 1987, 109, 6881-6883. Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063-1072.
13. (a) Evans, D. A.; Britton, T. C. J. Am. Chem. Soc. 1987, 109, 6881-6883. Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063-1072.
14. (b) Evans, D. A.; Evrard, D. A.; Rychnovsky, S. D.; Früh, T.; Whittingham, W. G.; DeVries, K. M. Tetrahedron Lett. 1992, 33, 1189-1192.
15. (c) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F., Jr. Tetrahedron 1988, 44, 5525-5540.
16. (d) Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394-6395.
17. (e) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395-6397.
18. (f) Trimble, L. A.; Vederas, J. C. J. Am. Chem. Soc. 1986, 108, 6397-6399.
19. (g) Loreto, M. A.; Pellacani, L.; Tardella, P. A. Tetrahedron Lett. 1989, 30, 2975-2978.
20. (h) Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 31, 991-994.
21. (a) Oppolzer, W. Tetrahedron 1987, 43, 1969-2004 and references therein.
22. (b) Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241-1250.
23. (c) Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293-318.
24. Capet, M.; David, F.; Bertin, L.; Hardy, J. C. Synth. Commun. 1995, 25, 3323-3327 and references therein.
25. Oppolzer, W.; Chapuis, C.; Bernardinelli, G. Helv. Chim. Acta 1984, 67, 1397-1401.
26. Morrison, J. D. Asymmetric Synthesis; Academic Press: 1984; Vol. 3.
27. (a) Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. Am. Chem. Soc. 1973, 95, 5065-5067.
28. (b) Bürgi, H. B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153-161.
29. Harmon, R. E.; Wellman, G.; Gupta, S. K. J. Org. Chem. 1973, 38, 11-16.
30. 19F NMR analysis.