Peptide-embedded heterocycles by mild single and multiple aza-Wittig ring closures

Angewandte Chemie - International Edition

Volumn 46, Issue 15, 2007, Pages 2701-2703

  Riedrich, Matthias ^a,b   Harkal, Surendra ^a,b   Arndt, Hans Dieter ^a,b  

^a TU DORTMUND UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

Author keywords

Azides; Azoles; Cyclization; Peptides; Wittig reactions

Indexed keywords

ESTERS; FUNCTIONAL GROUPS; NITROGEN COMPOUNDS; ORGANIC SOLVENTS;

AMINO ACID ESTERS; MULTIPLE RING CLOSURES; WITTIG REACTIONS;

AMINO ACIDS;

AZIDE; BIOLOGICAL PRODUCT; HETEROCYCLIC COMPOUND; PEPTIDE; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

AZIDES; AZOLES; BIOLOGICAL PRODUCTS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; PEPTIDES; STEREOISOMERISM;

EID: 34250879028     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604507     Document Type: Article

References (48)

1. Important reviews: a) P. Wipf, Chem. Rev. 1995, 95, 2115-2134;
2. b) R. S. Roy, A. M. Gehring, J. C. Milne, P. J. Belshaw, C. T. Walsh, Nat. Prod. Rep. 1999, 16, 249-263;
3. c) V. S. C. Yeh, Tetrahedron 2004, 60, 11 995-12 042;
4. d) E. Riego, D. Hernández, F. Albericio, M. Álvarez, Synthesis 2005, 1907-1922;
5. e) Z. Jin, Nat. Prod. Rep. 2006, 23, 464-496.
6. For broad reviews on the chemistry of 1,3-azoles, see: a) M. R. Grimmett in Comprehensive Heterocyclic Chemistry II, Vol. 3 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, pp. 77-220;
7. b) F. W. Hartner in Comprehensive Heterocyclic Chemistry II, Vol. 3 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, pp. 261-318;
8. c) A. Dondoni, P. Merino in Comprehensive Heterocyclic Chemistry II, Vol. 3 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, pp. 373-474.
9. a) H. Vorbrüggen, K. Krolikiewicz, Tetrahedron Lett. 1981, 22, 4471-4474;
10. b) A. I. Meyers, D. Hoyer, Tetrahedron Lett. 1985, 26, 4687-4690;
11. c) G. Burrell, J. M. Evans, G. E. Jones, G. Stemp, Tetrahedron Lett. 1990, 31, 3649-3653;
12. d) F. Yokokawa, Y. Hamada, T. Shioiri, Synlett 1992, 153-155;
13. e) P. Wipf, C. P. Miller, Tetrahedron Lett. 1992, 33, 907-910;
14. f) N. Galéotti, C. Montagne, J. Poncet, P. Jouin, Tetrahedron Lett. 1992, 33, 2807-2810;
15. g) M. A. Walker, C. H. Heathcock, J. Org. Chem. 1992, 57, 5566-5568;
16. h) A. B. Charette, P. Chua, J. Org. Chem. 1998, 63, 908-909;
17. i) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno, D. R. Williams, Org. Lett. 2000, 2, 1165-1168;
18. j) F. Yokokawa, T. Shioiri, Tetrahedron Lett. 2002, 43, 8679-8682;
19. k) S.-L. You, H. Razavi, J. W. Kelly, Angew. Chem. 2003, 115, 87-89;
20. Angew. Chem. Int. Ed. 2003, 42, 83-85;
21. l) A. Sakakura, R. Kondo, K. Ishihara, Org. Lett. 2005, 7, 1971-1974.
22. For a general review on azide chemistry, see: S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320-5374;
23. Angew. Chem. Int. Ed. 2005, 44, 5188-5240.
24. a) H. Staudinger, J. Meyer, Helv. Chim. Acta 1919, 2, 635-646;
25. b) Y. G. Gololobov, I. N. Zhmurova, L. F. Kasukhin, Tetrahedron 1981, 37, 431-412;
26. c) Y. G. Gololobov, L. F. Kasukhin, Tetrahedron 1992, 48, 1353-1406.
27. a) D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu, A. I. Meyers, J. Org. Chem. 1979, 44, 497-501;
28. b) M. North, G. Pattenden, Tetrahedron 1990, 46, 8267-8290;
29. c) A. I. Meyers, F. Tavares, Tetrahedron Lett. 1994, 35, 2481-2484;
30. d) D. R. Williams, P. D. Lowder, Y.-G. Yu, D. A. Brooks, Tetrahedron Lett. 1997, 38, 331-334.
31. a) For an overview, see: P. M. Fresneda, P. Molina, Synlett 2004, 1-17.
32. b) A stereoenriching aza-Wittig reaction has been reported recently: D. Lertpibulpanya, S. P. Marsden, I. Rodriguez-Garcia, C. A. Kilner, Angew. Chem. 2006, 118, 5122-5124;
33. Angew. Chem. Int. Ed. 2006, 45, 5000-5002.
34. Thiazoline: a) R. Brossmer, H. Mack, Tetrahedron Lett. 1981, 22, 933-936;
35. b) G. B. Kok, M. Campbell, B. Mackey, M. von Itzstein, J. Chem. Soc. Perkin Trans. 1 1996, 2811-2815;
36. c) J. Chen, C. J. Forsyth, Org. Lett. 2003, 5, 1281-1284;
37. Oxazoline: d) Yu. G. Gololobov, N. I. Gusar, M. P. Chaus, Tetrahedron 1985, 41, 793-799;
38. e) J. Mulzer, A. Meier, J. Buschmann, P. Luger, Synthesis 1996, 123-132;
39. f) H. Kato, K. Ohmori, K. Suzuki, Synlett 2001, 1003-1005;
40. g) K. C. Nicolaou, D. W. Kim, D. Schlawe, D. E. Lizos, R. G. de Noronha, D. A. Longbottom, Angew. Chem. 2005, 117, 5005-5009;
41. Angew. Chem. Int. Ed. 2005, 44, 4925-4929.
42. J. W Back, O. David, G. Kramer, G. Masson, P. T. Kasper, L. J. de Koning, L. de Jong, J. H. van Maarseveen, C. G. de Koster, Angew. Chem. 2005, 117, 8160-8164;
43. Angew. Chem. Int. Ed. 2005, 44, 7946-7950.
44. N. Kumagai, S. Matsunaga, M. Shibasaki, Angew. Chem. 2004, 116, 484-488;
45. Angew. Chem. Int. Ed. 2004, 43, 478-482.
46. P. B. Alper, S.-C. Hung, C.-H. Wong, Tetrahedron Lett. 1996, 37, 6029-6032.
47. Details will be disclosed elsewhere.
48. Although we have not witnessed any single indication for instabilities of the azides reported in this work, we strongly caution the use of appropriate protection measures during handling, especially when heating and/or concentrating azides of low molecular weight. See also reference [4].