Cyclopropyl building blocks in organic synthesis, 50. - An easy access to bicyclic peptides with an octahydro[2H]pyrazino[1,2-a]pyrazine skeleton

European Journal of Organic Chemistry

Volumn , Issue 6, 1999, Pages 1345-1356

  Belov, Vladimir N ^a,c   Funke, Christian ^a   Labahn, Thomas ^a   Es Sayed, Mazen ^b   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b BAYER AG   (Germany)

^c ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

Crystal structures; Diastereoselectivity; Octahydro 2H pyrazino 1,2 a pyrazine; Peptidomimetics; Tripeptides

Indexed keywords

ACETIC ACID DERIVATIVE; CYCLOPEPTIDE; ESTER; OCTAHYDRO[2H]PYRAZINO[1,2 A]PYRAZINE; PYRAZINE DERIVATIVE; TRIPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032783846     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199906)1999:6<1345::aid-ejoc1345>3.0.co;2-2     Document Type: Article

References (22)

1. [1a] T. Liese, F. Seyed-Mahdavi, A. de Meijere, Org. Synth. 1990, 69, 148-153.
2. [1b] M. Es-Sayed, C. Gratkowski, N. Krass, A. I. Meyers, A. de Meijere, Synlett 1992, 962-964.
3. [1c] M. Es-Sayed, C. Gratkowski, N. Krass, A. I. Meyers, A. de Meijere, Tetrahedron Lett. 1993, 34, 289-292.
4. [1d] M. Es-Sayed, T. Heiner, A. de Meijere, Synlett 1993, 57-58.
5. [1e] H. Primke, G. S. Sarin, S. Kohlstruk, G. Adiwidjaja, A. de Meijere, Chem. Ber. 1994, 127, 1051-1064.
6. [1f] L. Hadjiarapoglou, I. Klein, D. Spitzner, A. de Meijere, Synthesis 1996, 525-528.
7. [1g] A. de Meijere, L. Hadjiarapoglou, M. Noltemeyer, H.-J. Gutke, I. Klein, D. Spitzner, Eur. J. Org. Chem. 1998, 441-451. - Reviews:
8. [1h] A. de Meijere, L. Wessjohann, Synlett 1990, 20-32.
9. [1i] A. de Meijere in New Aspects of Organic Chemistry II, Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry - IKCOC 5, Kyoto Nov. 11-15, 1991, Y. Ohshiro, Z. Yoshida, Eds. Kodansha: Tokyo, 1992, 181-213.
10. For recent publications on peptidomimetics, see: [2a] M. A. Marx, A.-L. Grillot, C. T. Louer, K. A. Beaver, P. A. Bartlett, J. Am. Chem. Soc. 1997, 119, 6153-6167.
11. [2b] L. R. Smith, P. A. Bartlett, Molecules Online 1998, 2, 58-62.
12. [2c] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854.
13. [3a] M. Rink, K. Feiden, Arch. Pharm (Weinheim) 1962, 295, 121-126.
14. [3b] H. J. Beim, A. R. Day, J. Heterocycl. Chem. 1977, 14, 307-308.
15. [3c] S. Gubert, C. Braojos, A. Sacristán, J. A. Ortiz, Synthesis 1991, 318-320.
16. G. W. H. Cheseman in The Chemistry of Heterocyclic Compounds, 1979, Wiley, New York, pp. 575-582.
17. [5a] M. Robert, M. Barbier, E. Lederer, L. Roux, K. Biemann, W. Vetter, Bull. Soc. Chim. Fr. 1962, 187-188.
18. [5b] E. Hardegger, P. Liechti, L. M. Jackman, A. Boller, P. A. Plattner, Helv. Chim. Acta 1963, 60-74.
19. Further details of the crystal structure investigations may be obtained from the Fachinformationszentrum Karlsruhe, 76344 Eggenstein-Leopoldshafen (Germany), on quoting the deposit numbers CSD-410046, -410047, -410048, -410049, -410050 (e-mail: CRYSDATA@FIZ-Karsruhe.DE).
20. A. de Meijere, S. Teichmann, D. Yu, J. Kopf, M. Oly, N. von Thienen, Tetrahedron 1989, 45, 2957-2968.
21. G. M. Sheldrick, SHELXS-97, Program for Solution of Crystal Structures, University of Göttingen, Germany, 1997.
22. G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.