Small ring constrained pepfidomimetics. Synthesis of aziridine parallel β-sheet mimetics

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3857-3860

  Filigheddu, Silvia N ^a   Taddei, Maurizio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE DERIVATIVE; ACRYLIC ACID DERIVATIVE; AMINO ACID; AZIRIDINE DERIVATIVE; PEPTIDE;

ARTICLE; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032575193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00632-7     Document Type: Article

References (15)

1. 1. Kahn, M. Synlett, 1993, 821. Gante, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699.
2. 1. Kahn, M. Synlett, 1993, 821. Gante, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699.
3. 2. Nowick, J.S.; Smith, E.M.; Pairish, M. Chem. Soc. Rev. 1996, 25, 401 and references therein
4. 3. Nowick, J.S.; Holmes, D.L.; Mackin, G.; Noronha, G.; Shaka, A.J.; Smith, E.M. J. Am. Chem. Soc. 1996, 118, 2764. Smith, E.M., Holmes, D.L.; Shaka A.J.; Nowick, J.S. J. Org. Chem. 1997, 62, 7906 and references therein.
5. 3. Nowick, J.S.; Holmes, D.L.; Mackin, G.; Noronha, G.; Shaka, A.J.; Smith, E.M. J. Am. Chem. Soc. 1996, 118, 2764. Smith, E.M., Holmes, D.L.; Shaka A.J.; Nowick, J.S. J. Org. Chem. 1997, 62, 7906 and references therein.
6. 4. Mann, A.; Quaranta, L.; Reginato, G.; Taddei, M. Tetrahedron Lett. 1996, 37, 2651. Ciapetti, P.; Falorni, M.; Taddei, M. Tetrahedron 1996. 52, 7379.
7. 4. Mann, A.; Quaranta, L.; Reginato, G.; Taddei, M. Tetrahedron Lett. 1996, 37, 2651. Ciapetti, P.; Falorni, M.; Taddei, M. Tetrahedron 1996. 52, 7379.
8. 5. Nagel, D.L.; Woller, P.B.; Cromwell, N.H. J. Org. Chem. 1971, 36, 3911. For more recent references see: Garner, P.; Dogan, O.; Pillai, S. Tetrahedron Lett. 1994, 35, 1653. Cardillo, G.; Gentilucci, L. Tomassini, C.; Visa Castejon-Bordas, M.P. Tetrahedron Asymmetry 1996, 7, 755. For recent reviews on the synthesis of aziridines see: Osborn, H.M.I.; Sweeney, J. Tetrahedron Asymmetry 1997, 8, 1693. Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 68, 735.
9. 5. Nagel, D.L.; Woller, P.B.; Cromwell, N.H. J. Org. Chem. 1971, 36, 3911. For more recent references see: Garner, P.; Dogan, O.; Pillai, S. Tetrahedron Lett. 1994, 35, 1653. Cardillo, G.; Gentilucci, L. Tomassini, C.; Visa Castejon-Bordas, M.P. Tetrahedron Asymmetry 1996, 7, 755. For recent reviews on the synthesis of aziridines see: Osborn, H.M.I.; Sweeney, J. Tetrahedron Asymmetry 1997, 8, 1693. Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 68, 735.
10. 5. Nagel, D.L.; Woller, P.B.; Cromwell, N.H. J. Org. Chem. 1971, 36, 3911. For more recent references see: Garner, P.; Dogan, O.; Pillai, S. Tetrahedron Lett. 1994, 35, 1653. Cardillo, G.; Gentilucci, L. Tomassini, C.; Visa Castejon-Bordas, M.P. Tetrahedron Asymmetry 1996, 7, 755. For recent reviews on the synthesis of aziridines see: Osborn, H.M.I.; Sweeney, J. Tetrahedron Asymmetry 1997, 8, 1693. Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 68, 735.
11. 5. Nagel, D.L.; Woller, P.B.; Cromwell, N.H. J. Org. Chem. 1971, 36, 3911. For more recent references see: Garner, P.; Dogan, O.; Pillai, S. Tetrahedron Lett. 1994, 35, 1653. Cardillo, G.; Gentilucci, L. Tomassini, C.; Visa Castejon-Bordas, M.P. Tetrahedron Asymmetry 1996, 7, 755. For recent reviews on the synthesis of aziridines see: Osborn, H.M.I.; Sweeney, J. Tetrahedron Asymmetry 1997, 8, 1693. Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 68, 735.
12. 5. Nagel, D.L.; Woller, P.B.; Cromwell, N.H. J. Org. Chem. 1971, 36, 3911. For more recent references see: Garner, P.; Dogan, O.; Pillai, S. Tetrahedron Lett. 1994, 35, 1653. Cardillo, G.; Gentilucci, L. Tomassini, C.; Visa Castejon-Bordas, M.P. Tetrahedron Asymmetry 1996, 7, 755. For recent reviews on the synthesis of aziridines see: Osborn, H.M.I.; Sweeney, J. Tetrahedron Asymmetry 1997, 8, 1693. Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 68, 735.
13. 6. Marvel, C.S.; Cowan, J.C. J. Am. Chem. Soc. 1939, 61, 3156.
14. N2 mechanism. See Garner in ref. 5.
15. 8. A downfield shift on dilution may be reflective of an intramolecular hydrogen bond as, at this concentration, we assume that the values would be relative to unassociated molecules. Saunders, J.K.M.; Hunter, B.K. Modern NMR Spectroscopy, a Guide for Chemists. Oxford University Press, 1989, 208. The same approach was taken in ref. 3.