First synthesis of cyclotrihydrazino peptides

Chemical Communications

Volumn , Issue 15, 1997, Pages 1441-1442

  Carret, Sophie ^a   Baudy Floc'h, Michèle ^a   Robert, Albert ^a   Le Grel, Philippe ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004574307     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701932g     Document Type: Article

References (18)

1. A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244.
2. J. Gante, Synthesis, 1989, 405.
3. Y. A. Ovchinnikov and V. T. Ivanov, Tetrahedron, 1989, 31, 2177.
4. M. Bodanszky, Principles of Peptide Synthesis, Springer Verlag, 1984.
5. K. D. Kopple, J. Pharm. Sci., 1972, 61, 1345.
6. C. Barré, P. Le Grel, A. Robert and M. Baudy-Floc'h, J. Chem. Soc., Chem. Commun., 1994, 607.
7. Y. S. Klausner and M. Bodansky, Synthesis, 1974, 549.
8. M. Waki and N. Izumiyia, J. Am. Chem. Soc., 1967, 89, 1278.
9. R. Paul and G. W. Andersen, J Am. Chem. Soc., 1960, 82, 4596; B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl., 1978, 17, 522; B. Castro, J. R. Dormoy, G. Evin and C. Selve, Tetrahedron Lett., 1975, 1219; R. Knorr, A. Trzeciak, W. Bannwarth and D. Gillessen, Tetrahedron Lett., 1989, 30, 1927.
10. R. Paul and G. W. Andersen, J Am. Chem. Soc., 1960, 82, 4596; B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl., 1978, 17, 522; B. Castro, J. R. Dormoy, G. Evin and C. Selve, Tetrahedron Lett., 1975, 1219; R. Knorr, A. Trzeciak, W. Bannwarth and D. Gillessen, Tetrahedron Lett., 1989, 30, 1927.
11. R. Paul and G. W. Andersen, J Am. Chem. Soc., 1960, 82, 4596; B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl., 1978, 17, 522; B. Castro, J. R. Dormoy, G. Evin and C. Selve, Tetrahedron Lett., 1975, 1219; R. Knorr, A. Trzeciak, W. Bannwarth and D. Gillessen, Tetrahedron Lett., 1989, 30, 1927.
12. R. Paul and G. W. Andersen, J Am. Chem. Soc., 1960, 82, 4596; B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl., 1978, 17, 522; B. Castro, J. R. Dormoy, G. Evin and C. Selve, Tetrahedron Lett., 1975, 1219; R. Knorr, A. Trzeciak, W. Bannwarth and D. Gillessen, Tetrahedron Lett., 1989, 30, 1927.
13. Epoxides 1 were prepared in a two step procedure. For the first one, a Knoevenagel-Cope condensation, see P. D. Gardner and R. L. Brandon, J. Org. Chem., 1957, 22, 1704. For the second step, a stereospecific epoxidation of the alkene by sodium hypochlorite, see M. Baudy, A. Robert and A. Foucaud, J Org. Chem., 1978, 43, 3732.
14. Epoxides 1 were prepared in a two step procedure. For the first one, a Knoevenagel-Cope condensation, see P. D. Gardner and R. L. Brandon, J. Org. Chem., 1957, 22, 1704. For the second step, a stereospecific epoxidation of the alkene by sodium hypochlorite, see M. Baudy, A. Robert and A. Foucaud, J Org. Chem., 1978, 43, 3732.
15. P. Le Grel, M. Baudy-Floc'h and A. Robert, Synthesis, 1987, 306.
16. P. LeGrel, M. Baudy-Floc'h and A. Robert, Tetrahedron, 1988, 44, 4805.
17. M. M. Lenman, S. L. Ingham and D. Gani, Chem. Commun., 1996, 85.
18. M. Marraud, V. Dupont, V. Grand, S. Zerkout, A. Lecoq, G. Boussard, J. Vidal, A. Collet and A. Aubry, Biopolymers, 1993, 33, 1135.