A straightforward approach towards thiazoles and endothiopeptides via Ugi reaction

Organic and Biomolecular Chemistry

Volumn 3, Issue 17, 2005, Pages 3184-3187

  Kazmaier, Uli ^a   Ackermann, Stefanie ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; IRRADIATION; MICROWAVES; REACTION KINETICS;

ENDOTHIOPEPTIDES; ISONITRILES; MICROWAVE IRRADIATION; THIAZOLES;

AMINES;

PEPTIDE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; RADIATION EXPOSURE; STEREOISOMERISM; SYNTHESIS;

MICROWAVES; MOLECULAR STRUCTURE; PEPTIDES; STEREOISOMERISM; THIAZOLES;

EID: 25444442833     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b507028g     Document Type: Article

References (61)

1. (a) A. F. Spatola, in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, ed. B. Weinstein, Marcel Dekker, New York, 1983, vol. 7, ch. 5, pp. 267-357;
2. (b) Peptides; Chemistry and Biology, ed. N. Sewald and H.-D. Jakubke, Wiley-VCH, Weinheim, 2002, ch. 7, pp. 339-378.
3. Reviews: (a) R. Hirschmann, Angew. Chem., 1991, 103, 1305-1330;
4. R. Hirschmann, Angew. Chem., Int. Ed. Engl., 1991, 30, 1278-1301;
5. (b) A. Giannis and T. Kolter, Angew. Chem., 1991, 105, 1303-1326;
6. A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244-1267;
7. J. Gante, Angew. Chem., 1994, 106, 1780-1802;
8. J. Gante, Angew. Chem., Int. Ed. Engl., 1994, 33, 1699-1720.
9. D. Seebach, S. Y. Ko, H. Kessler, M. Köck, M. Reggelin, P. Schneider, M. D. Walkinshaw, J. J. Bolsterli and D. Beved, Helv. Chim. Acta, 1991, 74, 1953-1990.
10. (a) K. Clausen, A. F. Spatola, C. Lemieux, P. W. Schiller and S.O. Lawesson, Biochem. Biophys. Res. Commun., 1984, 120, 305-310;
11. (b) K. Clausen, M. Thorsen, S.-O. Lawesson and A. F. Spatola, J. Chem. Soc., Perkin Trans. 1, 1984, 785-798;
12. (c) G. Lajoie, F. Lepine, S. Lemaire, F. Jolicoeur, C. Aube, O. Turcotte and B. Belleau, Int. J. Pept. Protein Res., 1984, 24, 316-327.
13. C. I. Fincham, M. Higginbottom, D. R. Hill, D. C. Horwell, J. C. O'Toole, O. S. Ratcliffe, D. C. Rees and E. Roberts, J. Med Chem., 1992, 35, 1472-1484.
14. (a) P. A. Bartlett, K. L. Spear and N. E. Jacobsen, Biochemistry, 1982, 21, 1608-1611;
15. (b) P.Campbell and N.T. Nashed, J. Am. Chem. Soc., 1982, 104, 5221-5226.
16. H. Kessler, H. Matter, A. Geyer, H.-J. Diehl, M. Köck, G. Kurz, F. R. Opperdoes, M. Callens and R. K. Wierenga, Angew, Chem., 1992, 104, 343-345;
17. H. Kessler, H. Matter, A. Geyer, H.-J. Diehl, M. Köck, G. Kurz, F. R. Opperdoes, M. Callens and R. K. Wierenga, Angew. Chem., Int. Ed. Engl., 1992, 31, 328-330.
18. L. Maziak, O. Lajoie and B. Belleau, J. Am. Chem. Soc., 1986, 108, 182-183.
19. S. Yao, R. Zutshi and J. Chmielewski, Bioorg. Med. Chem. Lett., 1998, 8, 699-704.
20. W. E. Stewart and T. H. Siddall III, Chem. Rev., 1970, 70, 517-551.
21. (a) P. Wipf and P. C. Fritch, Tetrahedron Lett., 1994, 35, 5397-5400;
22. (b) C. D. J. Boden and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 2000, 875-882.
23. (a) M. North and G. Pattenden, Tetrahedron, 1990, 46, 8267-8290;
24. (b) L. A. McDonald, M. P. Foster, D. R. Phillips, C. M. Ireland, A. Y. Lee and J. Clardy, J. Org. Chem., 1992, 57, 4616-4624;
25. (c) For a review on biosynthesis see: R. S. Roy, A. M. Gehring, J. C. Milne, P. J. Belshaw and C. T. Walsh, Nat. Prod. Rep., 1999, 16, 249-263.
26. (a) J. P. Michael and G. Pattenden, Angew. Chem., 1993, 105, 1-24;
27. J. P. Michael and G. Pattenden, Angew. Chem., Int. Ed. Engl., 1993, 32, 1-23;
28. (b) J. R. Lewis, Nat. Prod. Rep., 1997, 14, 371-398.
29. (a) D. Schipper, J. Antibiot., 1983, 36, 1076-1077;
30. (b) W. D. Clark and P. Crews, Tetrahedron Lett., 1995, 36, 1185-1188;
31. (c) J. B. MacMillan, E. K. Trousdale and T. F. Molinski, Org. Lett., 2000, 2, 2721-2723.
32. (a) G. R. Pettit, J.-P. Xu, M. D. Williams, F. Hogan, J. M. Schmidt and R. L. Cerny, Bioorg. Med. Chem. Lett., 1997, 7, 827-832;
33. (b) G. R. Pettit, F. Hogan and D. L. Herald, J. Org. Chem., 2004, 69, 4019-4022.
34. (a) A. R. Carroll, Y. Feng, B. F. Bowden, F. Hogan, Q. L. Herald and J. C. Coll, J. Org. Chem., 1996, 61, 4059-4061;
35. (b) Y. Feng and B. F. Bowden, Aust. J. Chem., 1997, 50, 337-340.
36. K. Clausen, M. Thorsen and S.-O. Lawesson, Tetrahedron, 1981, 37, 3635-3639.
37. J. Jurayj and M. Cushman, Tetrahedron, 1992, 48, 8601-8614 and references cited.
38. (a) T. Hoeeg-Jenson, C. E. Olsen and A. Holm, J. Org. Chem., 1994, 59, 1257-1263;
39. (b) M. A. Shalaby, C.,W. Grote and H. Rapoport, J. Org. Chem., 1996, 61, 9045-9048.
40. (a) J. Lehmann, A. Linden and H. Heimgartner, Helv. Chim. Acta, 1999, 82, 888-908;
41. (b) J. Lehmann and H. Heimgartner, Helv. Chim. Acta, 1999, 82, 1899-1915.
42. C. Unverzagt, A. Geyer and H. Kessler, Angew. Chem., 1992, 104, 1231-1233;
43. C. Unverzagt, A. Geyer and H. Kessler, Angew. Chem., Int. Ed. Engl., 1992, 31, 1229-1230.
44. (a) S. Heck and A. Dömling, Synlett, 2000, 424-426;
45. (b) M. Umkehrer, J. Kolb, C. Burdack and W. Hiller, Synlett, 2005, 79-82;
46. A. Domling and K. Illgen, Synthesis, 2005, 662-667.
47. Reviews: (a) U. Kazmaier, Liebigs Ann./Recl, 1997, 285-295;
48. (b) U. Kazmaier, in Bioorganic Chemistry, ed. U. Diederichsen, T. K. Lindhorst, B. Westermann and L. A. Wessjohann, Wiley-VCH, Weinheim, 1999, pp. 201-206;
49. U. Kazmaier, S. Maier and F. L. Zumpe, Synlett, 2000, 1523-1535;
50. U. Kazmaier, in Claisen Rearrangements, ed. M. Hiersemann and U. Nubbemeyer, Wiley-VCH, Weinheim, 2005, pp. 231-297.
51. (a) I. Ugi, Isonitrile Chemistry, Academic press, New York, 1971;
52. (b) A. Dömling and I. Ugi, Angew. Chem., 2000, 112, 3300-3344;
53. A. Domling and I. Ugi, Angew. Chem., Int. Ed., 2000, 39, 3168-3210 and references cited therein.
54. (a) C. Hebach and U. Kazmaier, Chem. Commun., 2003, 596-597;
55. (b) U. Kazmaier and C. Hebach, Synlett, 2003, 1591-1594;
56. (c) U. Kazmaier and S. Ackermann, Synlett, 2004, 2576-2578;
57. (d) R. Pick, M. Bauer, U. Kazmaier and C. Hebach, Synlett, 2005, 757-760.
58. U. Kazmaier, C. Hebach, A. Watzke, S. Maier, H. Mues and V. Huch, Org. Biomol. Chem., 2005, 3, 136-145.
59. (a) P. A. Jacobi, M. Egbertson, R. F. Frechette, C. K. Miao and K. T. Weiss, Tetrahedron, 1988, 44, 3327-3338;
60. (b) D. M. Spero and S. R. Kapadia, Org. Chem., 1996, 61, 7398-7401.
61. M. E. Jung and M. A. Lyster, J. Org. Chem., 1977, 42, 3761-3764.