Application of reductive samariation to the synthesis of small unnatural peptides

Angewandte Chemie - International Edition

Volumn 39, Issue 1, 2000, Pages 242-246

  Ricci, Marina ^a   Madariaga, Leire ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Electron transfer; Peptides; Radicals; Reductions; Samarium

Indexed keywords

CARBONYL DERIVATIVE; GLYCOPEPTIDE; GLYCOSIDE; N ACETYLGALACTOSAMINE; N BROMOSUCCINIMIDE; PEPTIDE DERIVATIVE; PYRIDINE DERIVATIVE; SAMARIUM;

ALKYLATION; ARTICLE; BROMINATION; CHEMICAL MODIFICATION; CHEMICAL REACTION; DIASTEREOISOMER; PEPTIDE SYNTHESIS; PHOTOLYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0034598547     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000103)39:1<242::AID-ANIE242>3.0.CO;2-R     Document Type: Article

References (56)

1. For a comprehensive review on the use of peptide enolates by Seebach and co-workers, see D. Seebach, A. K. Beck, A. Studer in Modern Synthetic Methods, Vol. 7 (Eds.: B. Ernst, C. Leumann), VCH, Weinheim, 1995, pp. 1-178;
2. see also a) D. Seebach, H. G. Bossler, G. Gründler, S. Shoda, R. Wenger. Helv. Chim. Acta 1991, 74, 197;
3. b) D. Seebach, A. K. Beck, H. G. Bossler, C. Gerber, S. Y. Ko, C. W. Murtiashaw, R. Naef, S. Shoda, A. Thaler, M. Krieger, R. Wenger, Helv. Chim. Acta 1993, 76, 1564;
4. c) H. G. Bossler, D. Seebach, Helv. Chim. Acta 1994, 77, 1124;
5. d) D. Seebach, O. Bezençon, B. Jaun, T. Pietzonka, J. L. Matthews, F. N. M. Kühnle, W. B. Schweizer, Helv. Chim. Acta 1996, 79, 588;
6. e) T. Matt, D. Seebach, Helv. Chim. Acta 1998, 81, 1845, and references therein.
7. D. J. Ager, D. E. Froen, R. C. Klix, B. Zhi, J. McIntosh, R. Thangarasa, Tetrahedron 1994, 50, 1975.
8. a) M. J. O'Donnell, T. P. Burkholder, V. V. Khau, R. W. Roeske, Z. Tian, Pol. J. Chem. 1994, 68, 2477;
9. b) M. J. O'Donnell, C. Zhou, W. I., Scott, J. Am. Chem. Soc. 1996, 118, 6070.
10. a) U. Kazmaier, Angew. Chem. 1994, 106, 1046; Angew. Chem. Int. Ed. Engl. 1994, 33, 998;
11. a) U. Kazmaier, Angew. Chem. 1994, 106, 1046; Angew. Chem. Int. Ed. Engl. 1994, 33, 998;
12. b) U. Kazmaier, J. Org. Chem. 1994, 59, 6667;
13. c) U. Kazmaier, S. Maier, Chem. Commun. 1998, 2535;
14. d) U. Kazmaier, S. Maier, J. Org. Chem. 1999, 64, 4575.
15. a) C. J. Easton, I. M. Scharfbillig, E. W. Tan, Tetahedron Lett. 1988, 29, 1565;
16. b) C. J. Easton, E. W. Tan, M. P. Hay, J. Chem. Soc. Chem. Commun. 1989, 385;
17. c) V. A. Burgess, C. J. Easton, M. P. Hay, J. Am. Chem. Soc. 1989, 111, 1047.
18. A. Papadopoulos, B. Lewall, E. Steckhan, K.-D. Ginzel, F. Knoch, M. Nieger, Tetrahedron 1991, 47, 563.
19. For a recent review on peptide radicals, see C. J. Easton, Chem. Rev. 1997, 97, 53.
20. a) P. Renaud, D. Seebach, Angew. Chem. 1986, 98, 836; Angew. Chem. Int. Ed. Engl. 1986, 25, 843;
21. a) P. Renaud, D. Seebach, Angew. Chem. 1986, 98, 836; Angew. Chem. Int. Ed. Engl. 1986, 25, 843;
22. b) P. Renaud, D. Seebach, Helv. Chim. Acta 1986, 69, 1704;
23. c) D. Seebach, R. Charczuk, C. Gerber, P. Renaud, H. Berner, H. Schneider, Helv. Chim. Acta 1989, 72, 401.
24. W. Steglich, M. Jäger, S. Jaroch, P. Zistler, Pure Appl. Chem. 1994, 66, 2167.
25. a) D. Mazéas, T. Skrydstrup, J.-M. Beau, Angew. Chem. 1995, 107, 990; Angew. Chem. Int. Ed. Engl. 1995, 34, 909;
26. a) D. Mazéas, T. Skrydstrup, J.-M. Beau, Angew. Chem. 1995, 107, 990; Angew. Chem. Int. Ed. Engl. 1995, 34, 909;
27. b) O. Jarreton, T. Skrydstrup, J.-M. Beau, Chem. Commun. 1996, 1661;
28. c) D. Urban, T. Skrydstrup, C. Riche, A. Chiaroni, J.-M. Beau, Chem. Commun. 1996, 1883;
29. d) O. Jarreton, T. Skrydstrup, J.-M. Beau, Tetrahedron Lett. 1997, 38, 303;
30. e) T. Skrydstrup, C. Jarreton, D. Mazéas, D. Urban, J.-M. Beau, Chem. Eur. J. 1998, 4, 655;
31. f) D. Urban, T. Skrydstrup, J.-M. Beau, J. Org. Chem. 1998, 63, 2507;
32. g) L. Andersen, L. M. Mikkelsen, J.-M. Beau, T. Skrydstrup, Synlett 1998, 1393;
33. h) O. Jarreton, T. Skrydstrup, J.-M. Beau, Chem. Eur. J. 1999, 5, 430;
34. i) S. L. Krintel, J. Jiménez-Barbero, T. Skrydstrup, Tetrahedron Lett. 1999, 40, 7565.
35. 2 in organic synthesis, see A. Krief, A.-M. Laval, Chem. Rev. 1999, 99, 745; G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321; T. Skrydstrup, Angew Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 345.
36. 2 in organic synthesis, see A. Krief, A.-M. Laval, Chem. Rev. 1999, 99, 745; G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321; T. Skrydstrup, Angew Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 345.
37. 2 in organic synthesis, see A. Krief, A.-M. Laval, Chem. Rev. 1999, 99, 745; G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321; T. Skrydstrup, Angew Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 345.
38. 2 in organic synthesis, see A. Krief, A.-M. Laval, Chem. Rev. 1999, 99, 745; G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321; T. Skrydstrup, Angew Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 345.
39. 2 in organic synthesis, see A. Krief, A.-M. Laval, Chem. Rev. 1999, 99, 745; G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321; T. Skrydstrup, Angew Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 345.
40. B. Giese, H.-G. Zetz in Preparative Carbohydrate Chemistry (Ed.: S. Hanessian), Marcel Dekker, New York, 1997, p. 507, and references therein.
41. Since only two diastereomers were isolated in the condensation of 6b with cyclohexanone, it does not appear that epimerization is occurring at the adjacent amino acid moieties under the reaction conditions used.
42. See also a) M. Kawatsura, F. Dekura, H. Shirahama, F. Matsuda, Synlett 1996, 373;
43. b) G. A. Molander, J. C. McWilliams, B. C. Noll, J. Am. Chem. Soc. 1997, 119, 1265.
44. 2-coordinated ketone or aldehyde. The carbonyl group should display a greater reactivity due to a lowered LUMO, while the high-energy oxy radical intermediate formed upon radical addition would be immediately reduced by the presence of the divalent lanthanide. Nevertheless, evidence against radical-type mechanisms for carbonyl addition reactions have been put forth for other systems. For a discussion on this topic, see D. P. Curran, T. L. Fevig, C. P. Jasperse, M. J. Totleben, Synlett 1992, 943, and references therein.
45. For some recent approaches to the synthesis of C-glycosyl amino acids and peptides, see a) F. Burkhart, M. Hoffmann, H. Kessler, Angew. Chem. 1997, 109, 1240; Angew. Chem. Int. Ed. Engl. 1997, 36, 1191;
46. For some recent approaches to the synthesis of C-glycosyl amino acids and peptides, see a) F. Burkhart, M. Hoffmann, H. Kessler, Angew. Chem. 1997, 109, 1240; Angew. Chem. Int. Ed. Engl. 1997, 36, 1191;
47. b) L. Lay, M. Meldal, F. Nicotra, L. Panza, G. Russo, Chem. Commun. 1997, 1469;
48. c) S. D. Debenham, J. S. Debenham, M. J. Burk, E. J. Toone, J. Am. Chem. Soc. 1997, 119, 9897;
49. d) A. Dondoni, A. Marra, A. Massi, Chem. Commun. 1998, 1741;
50. e) A. Dondoni, A. Marra, A. Massi, Tetrahedron Lett. 1998, 39, 6601;
51. f) A. Dondoni, A. Marra, A. Massi, Tetrahedron 1998, 54, 2827;
52. g) R. N. Ben, A. Orellana, P. Arya, J. Org. Chem. 1998, 63, 4817;
53. h) P. Arya, R. N. Ben, H. Qin, Tetrahedron Lett. 1998, 39, 6131;
54. i) D. Urban, T. Skrydstrup, J.-M. Beau, Chem. Commun. 1998, 955;
55. j) A. J. Pearce, S. Ramaya, S. N. Thorn, G. B. Bloomberg, D. S. Walter, T. Gallagher, J. Org. Chem. 1999, 64, 5453.
56. Prepared in two steps from methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside, by first allylation with allyltrimethylsilane and TMSOTf and then ozonolysis: A. Hosomi, Y. Sakata, H. Sakurai, Carbohydrate Res. 1987, 171, 125.