Cyclic dipeptides. 2. A simple synthesis of methyl (6R)-6-tert-butoxycarbonylamino-4,5,6,7-tetrahydro-2-methyl-5-oxo-1,4 -thiazepine-3-carboxylate, A useful intermediate for the preparation of potential antihypertensive agents

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2775-2778

  Botta, Maurizio ^a   Crescenza, Angela ^a   Magara, Walter ^a   Corelli, Federico ^a  

^a UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIHYPERTENSIVE AGENT; CYCLOPEPTIDE; DIPEPTIDE; TEMOCAPRIL; THIAZEPINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030964816     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00468-1     Document Type: Article

References (17)

1. F. Corelli, A. Crescenza, D. Dei, M. Taddei, M. Botta, Tetrahedron: Asymmetry, 1994, 5, 1469.
2. (a) J. Gante, Angew. Chem. Int. Ed. Engl., 1994, 33, 1699.
3. (b) G. L. Olson, D. R. Bolin, M. P. Bonner, M. Boes, C. M. Cook, D. C, Fry, B. J. Graves, M. Hatada, D. E. Hill, M. Kahn, V. S. Madison, V. K. Rusiecki, R. Sarabu, J. Sepinwall, G. P. Vincent, M. E. Voss, J. Med. Chem., 1993, 36, 3039.
4. A. Giannis, T. Kolter, Angew. Chem. Int. Ed. Engl., 1993, 32, 1244.
5. C. A. Fink, J. E. Carlson, P. A. McTaggart, Y. Qiao, R. Webb, R. Chatelain, A. Y. Jeng, A. J. Trapani, J. Med. Chem. 1996, 39, 3158.
6. X-M. Cheng, In Annu. Rep. Med. Chem., V. 30; Bristol, J. A., Ed.; Academic Press: San Diego, U.S.A., 1995; p. 295.
7. (a) A. Garofalo, G. Balconi, M. Botta, F. Corelli, M. D'Incalci, G. Fabrizi, I. Fiorini, D. Lamba, V. Nacci, Eur. J. Med. Chem., 1993, 28, 213.
8. (b) G. Campiani, A. Garofalo, I. Fiorini, M. Botta, V. Nacci, A. Tafi, A. Chiarini, R. Budriesi, G. Bruni, M. R. Romeo, J. Med. Chem., 1995, 38, 4393.
9. (c) F. Corelli, F. Manetti, A. Tafi, G. Campiani, V. Nacci, M. Botta, J. Med. Chem., 1997, 40, 125.
10. (a) G. Delle Monache, B. Botta, F. Delle Monache, R. Espinal, S. C. De Bonnevaux, C. De Luca, M. Botta, F. Corelli, M. Carmignani, J. Med. Chem., 1993, 36, 2956.
11. (b) F. Corelli, D. Dei, G. Delle Monache, B. Botta, C. De Luca, M. Carmignani, A. R. Volpe, M. Botta, Bioorg. Med. Chem. Lett., 1996, 6, 653 and references cited therein.
12. 1 prepared from L-threonine led to the same olefin 6.
13. W. Magara, doctorate thesis, University of Siena, 1995.
14. See for example: (a) R. H. Summerville, P. V. R. Schleyer, J. Am. Chem. Soc., 1972, 94, 3629.
15. (b) T. C. Clarke, D. R. Kelsey, R. G. Bergman, J. Am. Chem. Soc, 1972, 94, 3626.
16. No attempt has been yet made to assess the actual mechanism of the cyclization reaction.
17. 1H NMR spectroscopy. All the new compounds gave satisfactory (±0.4% of the theoretical values) elementary analyses, with the only exception of 4 which resulted too unstable to be analyzed.