Peptide syntheses via Ugi reactions with ammonia

Synlett

Volumn , Issue 11, 2003, Pages 1591-1594

  Kazmaier, Uli ^a   Hebach, Christina ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Ammonia; Peptides; Six component coupling; Ugi reactions

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; AMINE; AMMONIA; CARBOXYLIC ACID DERIVATIVE; PEPTIDE; TRIFLUOROETHANOL;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CRYSTALLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; UGI REACTION;

EID: 0041409732     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40987     Document Type: Article

References (42)

1. (a) Wagner, I.; Musso, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 816; Angew. Chem. 1983, 95, 827.
2. (a) Wagner, I.; Musso, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 816; Angew. Chem. 1983, 95, 827.
3. (b) Annual reports, In Amino Acids, Peptides and Proteins, Specialist Periodical Reports, Chem. Soc.: London
4. (c) Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1.
5. Gräfe, U. Biochemie der Antibiotika; Spektrum: Heidelberg, 1992.
6. (a) Barluenga, J.; Campos, P. J.; Gonzáles, C. M.; Suárez, J. C. J. Org. Chem. 1991, 56, 2234.
7. (b) Marshall, R. G. Tetrahedron 1993, 49, 3547.
8. (a) Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods, Vol. 7; Ernst, B.; Leumann, C., Eds.; VCH: Weinheim, 1995, 1.
9. (b) Kazmaier, U.; Maier, S. J. Org. Chem. 1999, 64, 4574.
10. (a) Ugi, I. Isonitrile Chemistry; Academic Press: New York, 1971.
11. (b) Ugi, I. Chem.-Ztg. 1997, 74, 9.
12. (c) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168; Angew. Chem. 2000, 112, 3300 and references cited therein.
13. (c) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168; Angew. Chem. 2000, 112, 3300 and references cited therein.
14. (a) Ugi, I.; Steinbrückner, C. Chem. Ber. 1961, 94, 2797.
15. (b) Keating, T. A.; Armstrong, R. W. J. Org. Chem. 1998, 63, 867.
16. Ugi, I.; Offermann, K. Chem. Ber. 1964, 97, 2996.
17. Ugi, I.; Offermann, K.; Herlinger, H.; Marqharding, D. Liebigs Ann. Chem. 1967, 709, 1.
18. (a) Urban, R.; Ugi, I. Angew. Chem. 1975, 87, 67.
19. (b) Siegmüller, F.; Ugi, I. Tetrahedron 1986, 42, 5931.
20. (a) Kunz, H.: Pfrengle, W. J. Am. Chem. Soc. 1988, 110, 651.
21. (b) Kunz, H.; Pfrengle, W.; Sager, W. Tetrahedron Lett. 1989, 30, 4109.
22. (c) Lehnhoff, S.; Goebel, M.; Karl, R. M.; Klösel, R.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 1104; Angew. Chem. 1995, 107, 1208.
23. (c) Lehnhoff, S.; Goebel, M.; Karl, R. M.; Klösel, R.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 1104; Angew. Chem. 1995, 107, 1208.
24. (d) Ziegler, T.; Kaiser, H.; Schlömer, R.; Koch, C. Tetrahedron 1999, 55, 8397.
25. (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem. Int. Ed. 2000, 39, 1431; Angew. Chem. 2000, 112, 1489.
26. (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem. Int. Ed. 2000, 39, 1431; Angew. Chem. 2000, 112, 1489.
27. Tempest, P. A.; Brown, S. D.; Armstrong, R. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 460; Angew. Chem. 1996, 108, 689.
28. Tempest, P. A.; Brown, S. D.; Armstrong, R. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 460; Angew. Chem. 1996, 108, 689.
29. Hebach, C.; Kazmaier, U. Chem. Commun. 2003, 596.
30. (a) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855.
31. (b) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364.
32. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606.
33. (d) Williams, R. M.; Liu, J. J. Org. Chem. 1998, 63, 2130.
34. (e) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133.
35. (f) Cabrejas, L. M. M.; Rohrbach, S.; Wagner, D.; Kallen, J.; Zenke, G.; Wagner, J. Angew. Chem. Int. Ed. 1999, 38, 2443; Angew. Chem. 1999, 111, 2595.
36. (f) Cabrejas, L. M. M.; Rohrbach, S.; Wagner, D.; Kallen, J.; Zenke, G.; Wagner, J. Angew. Chem. Int. Ed. 1999, 38, 2443; Angew. Chem. 1999, 111, 2595.
37. 2O), 3.85 (dd, J = 17.9, 3.7 Hz, 1 H), 4.05 (dd, J = 17.8, 3.8 Hz, 1 H), 4.41 (m, 1 H), 7.31-7.73 (m, 5 H), 7.57-7.78 (m, 2 H).
38. 3): ° = 0.72 (d, J = 6.7 Hz, 3 H), 0.75 (d, J = 6.7 Hz, 3 H), 1.01 (d, J = 6.6 Hz, 3 H), 1.03 (d, J = 6.6 Hz, 3 H), 2.08 (m, 1 H), 2.98 (m, 1 H), 3.31 (s, 3 H), 3.59 (d, J = 11.2 Hz, 1 H), 3.70 (s, 3H), 3.94 (dd, J = 15.2, 2.5 Hz, 1 H), 4.01-4. 16 (m, 2 H), 7.32-7.40 (m, 5 H), 8.95 (bs, 1 H).
39. br, 1 H), 6.63 (d, 1 H, J = 7.5 Hz), 7.39-7.53 (m, 5 H), 7.79-7.82 (m, 2 H).
40. Floyd, C. D.; Harnett, L. A.; Miller, A.; Patel, S.; Saroglou, L.; Whittaker, M. Synlett 1998, 637.
41. 4 and evaporation of the solvent gave the crude peptide, which was purified flash chromatography. The diastereomers were separated by preparative medium pressure chromatography on silica (LiChroprep Si60) using EtOAc/hexanes as eluents.
42. br, acidic H's), 7.48-7.65 (m, 3 H), 7.82-7.99 (m, 2 H).