Application of the peptide Claisen rearrangement toward the synthesis of cyclic peptides

Organic Letters

Volumn 1, Issue 11, 1999, Pages 1763-1766

  Kazmaier, Uli ^a   Maier, Sabine ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001477716     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9910262     Document Type: Article

References (51)

1. Amino Acids, Peptides and Proteins; Specialist Periodical Reports; Chemical Society: London.
2. Gräfe, U. Biochemie der Antibiotika; Spektrum: Heidelberg, 1992. Antibiotics and Antiviral Compounds; Krohn, K., Kirst, H. A., Maag, H., Eds.; VCH: Weinheim, 1993.
3. Gräfe, U. Biochemie der Antibiotika; Spektrum: Heidelberg, 1992. Antibiotics and Antiviral Compounds; Krohn, K., Kirst, H. A., Maag, H., Eds.; VCH: Weinheim, 1993.
4. Mutschler, E. Arzneimittelwirkungen; Wissenschaftliche Verlagsgesellschaft: Stuttgart, 1991. Eberle, A. E. Chimia 1991, 45, 145.
5. Mutschler, E. Arzneimittelwirkungen; Wissenschaftliche Verlagsgesellschaft: Stuttgart, 1991. Eberle, A. E. Chimia 1991, 45, 145.
6. Musiol, H.-J.; Siedler, F.; Quarzago, D.; Moroder, L. Biopolymers 1994, 34, 1553. Siedler, F.; Quarzago, D.; Rudolph-Bohner, S.; Moroder, L. Biopolymers 1994, 34, 1563.
7. Musiol, H.-J.; Siedler, F.; Quarzago, D.; Moroder, L. Biopolymers 1994, 34, 1553. Siedler, F.; Quarzago, D.; Rudolph-Bohner, S.; Moroder, L. Biopolymers 1994, 34, 1563.
8. Rizo, J.; Gierasch, L. M. Annu. Rev. Biochem. 1992, 61, 387.
9. Reviews: Tetrahedron Symposia-in-print 50 (Kahn, M. Ed.; 1993. Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303; Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
10. Reviews: Tetrahedron Symposia-in-print 50 (Kahn, M. Ed.; 1993. Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303; Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
11. Reviews: Tetrahedron Symposia-in-print 50 (Kahn, M. Ed.; 1993. Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303; Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
12. Nutt, R. F.; Veber, D. F.; Saperstein, R. J. Am. Chem. Soc. 1980, 102, 6539.
13. Nutt, R. F.; Strachan, R. G.; Veber, D. F.; Holly, F. W. J. Org. Chem. 1980, 45, 3078. Williams, R. M.; Yan, C. J. Org. Chem. 1992, 57, 6519. Bold, G.; Allmendinger, T.; Herold, P.; Moesch, L.; Schär, H. P.; Duthaler, R. O. Helv. Chim. Acta 1992, 75, 865. Lange, M.; Fischer, P. M. Helv. Chim. Acta 1998, 81, 2053.
14. Nutt, R. F.; Strachan, R. G.; Veber, D. F.; Holly, F. W. J. Org. Chem. 1980, 45, 3078. Williams, R. M.; Yan, C. J. Org. Chem. 1992, 57, 6519. Bold, G.; Allmendinger, T.; Herold, P.; Moesch, L.; Schär, H. P.; Duthaler, R. O. Helv. Chim. Acta 1992, 75, 865. Lange, M.; Fischer, P. M. Helv. Chim. Acta 1998, 81, 2053.
15. Nutt, R. F.; Strachan, R. G.; Veber, D. F.; Holly, F. W. J. Org. Chem. 1980, 45, 3078. Williams, R. M.; Yan, C. J. Org. Chem. 1992, 57, 6519. Bold, G.; Allmendinger, T.; Herold, P.; Moesch, L.; Schär, H. P.; Duthaler, R. O. Helv. Chim. Acta 1992, 75, 865. Lange, M.; Fischer, P. M. Helv. Chim. Acta 1998, 81, 2053.
16. Nutt, R. F.; Strachan, R. G.; Veber, D. F.; Holly, F. W. J. Org. Chem. 1980, 45, 3078. Williams, R. M.; Yan, C. J. Org. Chem. 1992, 57, 6519. Bold, G.; Allmendinger, T.; Herold, P.; Moesch, L.; Schär, H. P.; Duthaler, R. O. Helv. Chim. Acta 1992, 75, 865. Lange, M.; Fischer, P. M. Helv. Chim. Acta 1998, 81, 2053.
17. Williams, R. M.; Liu, J. J. Org. Chem. 1998, 63, 2130.
18. O'Leary, D. J.; Miller, S. J.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 1689.
19. Reviews; Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. Koert, U. Nachr. Chem. Tech. Lab. 1995, 43, 809. Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124; Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
20. Reviews; Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. Koert, U. Nachr. Chem. Tech. Lab. 1995, 43, 809. Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124; Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
21. Reviews; Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. Koert, U. Nachr. Chem. Tech. Lab. 1995, 43, 809. Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124; Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
22. Reviews; Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. Koert, U. Nachr. Chem. Tech. Lab. 1995, 43, 809. Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124; Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
23. Reviews; Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. Koert, U. Nachr. Chem. Tech. Lab. 1995, 43, 809. Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124; Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
24. Reviews; Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. Koert, U. Nachr. Chem. Tech. Lab. 1995, 43, 809. Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124; Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
25. Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606.
26. Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. Pernerstorfer, J.; Schuster, M.; Blechert, S. J. Chem. Soc., Chem. Commun. 1997, 1949. Ripka, A. S.; Bohacek, R. S.; Rich, D. H. Bioorg. Med. Chem. Lett. 1998, 8, 357. Cabrejas, L. M. M.; Rohrbach, S.; Wagner, D.; Kallen, J.; Zenke, G.; Wagner, J. Angew. Chem. 1999, 111, 2595; Angew. Chem., Int. Ed. Engl. 1999, 38, 2443.
27. Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. Pernerstorfer, J.; Schuster, M.; Blechert, S. J. Chem. Soc., Chem. Commun. 1997, 1949. Ripka, A. S.; Bohacek, R. S.; Rich, D. H. Bioorg. Med. Chem. Lett. 1998, 8, 357. Cabrejas, L. M. M.; Rohrbach, S.; Wagner, D.; Kallen, J.; Zenke, G.; Wagner, J. Angew. Chem. 1999, 111, 2595; Angew. Chem., Int. Ed. Engl. 1999, 38, 2443.
28. Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. Pernerstorfer, J.; Schuster, M.; Blechert, S. J. Chem. Soc., Chem. Commun. 1997, 1949. Ripka, A. S.; Bohacek, R. S.; Rich, D. H. Bioorg. Med. Chem. Lett. 1998, 8, 357. Cabrejas, L. M. M.; Rohrbach, S.; Wagner, D.; Kallen, J.; Zenke, G.; Wagner, J. Angew. Chem. 1999, 111, 2595; Angew. Chem., Int. Ed. Engl. 1999, 38, 2443.
29. Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. Pernerstorfer, J.; Schuster, M.; Blechert, S. J. Chem. Soc., Chem. Commun. 1997, 1949. Ripka, A. S.; Bohacek, R. S.; Rich, D. H. Bioorg. Med. Chem. Lett. 1998, 8, 357. Cabrejas, L. M. M.; Rohrbach, S.; Wagner, D.; Kallen, J.; Zenke, G.; Wagner, J. Angew. Chem. 1999, 111, 2595; Angew. Chem., Int. Ed. Engl. 1999, 38, 2443.
30. Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. Pernerstorfer, J.; Schuster, M.; Blechert, S. J. Chem. Soc., Chem. Commun. 1997, 1949. Ripka, A. S.; Bohacek, R. S.; Rich, D. H. Bioorg. Med. Chem. Lett. 1998, 8, 357. Cabrejas, L. M. M.; Rohrbach, S.; Wagner, D.; Kallen, J.; Zenke, G.; Wagner, J. Angew. Chem. 1999, 111, 2595; Angew. Chem., Int. Ed. Engl. 1999, 38, 2443.
31. Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. Pernerstorfer, J.; Schuster, M.; Blechert, S. J. Chem. Soc., Chem. Commun. 1997, 1949. Ripka, A. S.; Bohacek, R. S.; Rich, D. H. Bioorg. Med. Chem. Lett. 1998, 8, 357. Cabrejas, L. M. M.; Rohrbach, S.; Wagner, D.; Kallen, J.; Zenke, G.; Wagner, J. Angew. Chem. 1999, 111, 2595; Angew. Chem., Int. Ed. Engl. 1999, 38, 2443.
32. Review: Kazmaier, U. Liebigs Ann./Recl. 1997, 285 and references therein.
33. Kazmaier, U. Angew. Chem. 1994, 106, 1046; Angew. Chem., Int. Ed. Engl. 1994, 33, 998.
34. Kazmaier, U. Angew. Chem. 1994, 106, 1046; Angew. Chem., Int. Ed. Engl. 1994, 33, 998.
35. Kazmaier, U.; Schneider, C. Synlett, 1996, 975. Kazmaier, U.; Schneider, C. Synthesis 1998, 1321.
36. Kazmaier, U.; Schneider, C. Synlett, 1996, 975. Kazmaier, U.; Schneider, C. Synthesis 1998, 1321.
37. Kazmaier, U. J. Org. Chem. 1994, 59, 6667.
38. Kazmaier, U.; Maier, S. J. Chem. Soc., Chem. Commun. 1998, 2535.
39. Kazmaier, U.; Maier, S. J. Org. Chem. 1999, 64, 4574.
40. Zumpe, F. L.; Kazmaier, U. Synlett 1998, 1199. Zumpe, F. L.; Kazmaier, U. Synthesis, in press.
41. Zumpe, F. L.; Kazmaier, U. Synlett 1998, 1199. Zumpe, F. L.; Kazmaier, U. Synthesis, in press.
42. General Procedure for Peptide Claisen Rearrangements: A total of 0.2 mmol of the corresponding peptide ester were dissolved in 4 mL of THF, before 0.4 mmol (380 mg) of tin chloride were added. The mixture was cooled to -70°C. A freshly prepared solution of 1 mmol LHMDS in 2.5 mL of THF was added slowly, and the reaction mixture was allowed to warm to room temperature overnight. The resulting solution was hydrolyzed by vigorous stirring for 1 h with 5 mL of 1 N HCl solution. After separation of the aqueous layer the rearrangement product was extracted three times with 10 mL of 1 N NaOH solution. The combined basic aqueous layers were acidified with 1 N HCl solution (pH 1), and the peptide was extracted twice with methylene chloride (15 mL each). After evaporation of the solvent, the crude product was converted into the corresponding methyl esters with diazomethane and purified by flash chromatography.
43. The stereochemical outcome of this reaction probably can be explained by a 4-fold coordination of the deprotonated peptide chain toward the chelating metal ion. In such a complex, one face of the enolate is shielded by the isopropyl side chain of the (S)-valine. Claisen rearrangement obviously occurs from the "opposite" face giving rise to an (R)-amino acid. See also ref 19.
44. General Procedure for the N-Allylations of Peptides. To a stirred solution of the Ts-protected peptide (1 mmol) in 2 mL of dry THF a solution of π-allylpalladium chloride dimer (0.01 mmol), triphenylphosphine (0.045 mmol), and the allyl carbonate (2 mmol) was added at room temperature. The solution was stirred overnight. After evaporation of the solvent, the residue was purified by flash chromatography.
45. No reaction was observed, even at temperatures up to 90°C. These conditions only resulted in decomposition of the catalyst.
46. The newly generated amino acid was formed in racemic form, because proline containing peptides do not undergo stereoselective Claisen rearrangements (see ref 19).
47. 2 under argon. The clear solution was refluxed overnight. The solvent was removed in vacuo, and the residue was purified by flash chromatography.
48. 1H NMR spectrum.
49. The (E) isomer was formed preferentially (J = 15.4 Hz), which could be purified by crystallization.
50. Unfortunately, the olefin geometry could not be determined from the NMR spectra.
51. Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989. 30, 1927.