Direct entry to peptidyl ketones via SmI2-mediated C-C bond formation with readily accessible N-peptidyl oxazolidinones

Journal of Organic Chemistry

Volumn 73, Issue 3, 2008, Pages 1088-1092

  Mittag, Tina ^a   Christensen, Kasper L ^a   Lindsay, Karl B ^a   Nielsen, Niels Christian ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL BONDS; ELECTRONS; PEPTIDES; SYNTHESIS (CHEMICAL);

BOND FORMATION; FUNCTIONALIZATION; PEPTIDYL KETONES;

KETONES;

ALKENE DERIVATIVE; IODINE DERIVATIVE; KETONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; SAMARIUM;

ADDITION REACTION; ARTICLE; COVALENT BOND; DIASTEREOISOMER; REACTION ANALYSIS; SYNTHESIS;

ACRYLAMIDES; AMINES; AMINO ACIDS; CARBON; FREE RADICALS; IODIDES; KETONES; MOLECULAR STRUCTURE; OXAZOLIDINONES; PEPTIDES; SAMARIUM;

EID: 38849103735     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702286b     Document Type: Article

References (29)

1. For some recent reviews, see: (a) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305.
2. (b) Powers, J. C.; Asgian, J. L.; Ekici, Ö. D.; James, K. E. Chem. Rev. 2002, 102, 4639.
3. See: Våbenø, J.; Nielsen, U.; Ingebrigtsten, T.; Lejon, T.; Steffansen, B.; Luthman, K. J. Med. Chem. 2004, 47, 4755 and references cited therein.
4. Baratt, B. J. W.; Easton, C. J.; Henry, J. D.; Li, I. H. W.; Random, L.; Simpson, J. S. J. Am. Chem. Soc. 2004, 126, 13306.
5. For a few representative examples see: (a) DeGraw, J. I.; Almquist, R. G.; Hiebert, C. K.; Colwell, W. T.; Crase, J.; Hayano, T.; Judd, A. K.; Dousman, L.; Smith, R. L.; Waud, W. R.; Uchida, I. J. Med. Chem. 1997, 40, 2386.
6. (b) Eda, M.; Ashimori, A.; Akahoshi, F.; Yoshimura, T.; Inoue, Y.; Fukaya, C.; Nakajima, M.; Fukuyama, H.; Imada, T.; Nakamura, N. Bioorg. Med. Chem. Lett. 1998, 8, 913.
7. (c) Dragovich, P. S.; Zhou, R.; Webber, S. E.; Prins, T. J.; Kwok, A. K.; Okano, K.; Fuhrman, S. A.; Zalman, L. S.; Maldonado, F. C.; Brown, E. L.; Meador, J. W., III; Patick, A. K.; Ford, C. E.; Brothers, M. A.; Binford, S. L.; Matthews, D. A.; Ferre, R. A.; Worland, S. T. Bioorg. Med. Chem. Lett. 2000, 10, 45.
8. Yang, H.; Li. H.; Wittenberg, R.; Egi. M.; Huang, W.; Liebeskind, L. J. Am. Chem. Soc. 2007, 129, 1132.
9. For an interesting partial approach to peptidyl ketones, see: Lin, W.; Tryder, N.; Su, F.; Zercher, C. K.; Jasinski, J. P.; Butcher, R. J. J. Org. Chem. 2006, 71, 8140.
10. 2-promoted coupling reactions of amino acid thioesters see: (a) Blakskjær, P.; Høj, B.; Riber, D.; Skrydstrup, T. J. Am. Chem. Soc. 2003, 125, 4030.
11. (b) Mikkelsen, L. M.; Jensen, C. M.; Høj, B.; Blakskjær, P.; Skrydstrup, T. Tetrahedron 2003, 59, 10541.
12. (c) Jensen, C. M.; Lindsay, K. B.; Andreasen, P.; Skrydstrup, T. J. Org. Chem. 2005, 70, 7512.
13. (d) Lindsay, K. B.; Skrydstrup, T. J. Org. Chem. 2006, 71, 4766.
14. 2 in organic synthesis, see: (a) Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371.
15. (b) Kagan, H. B. Tetrahedron 2003, 59, 10351.
16. (c) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
17. (d) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745.
18. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321.
19. (f) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
20. 2-promoted N-acyloxazolidinone coupling reactions see: (a) Jensen, C. M.; Lindsay, K. B.; Taaning, R. H.; Karaffa, J.; Hansen, A. M.; Skrydstrup, T. J. Am. Chem. Soc. 2005, 127, 6544.
21. (b) Hansen, A. M.; Lindsay, K. B.; Sudhadevi Antharjanam, P. K.; Karaffa, J.; Daasbjerg, K.; Flowers, R. A., II; Skrydstrup, T. J. Am. Chem. Soc. 2006, 128, 9616.
22. (a) Karaffa, J.; Lindsay, K. B.; Skrydstrup, T. J. Org. Chem. 2006, 71, 8219.
23. (b) Lindsay, B. K.; Ferrando, F.; Christensen, K. L.; Overgaard, J.; Roca, T.; Bennasar, M.-L.; Skrydstrup, T. J. Org. Chem. 2007, 72, 4181.
24. (a) Bänteli, R.; Brun, I.; Hall, P.; Metternich, R. Tetrahedron Lett. 1999, 40, 2109-2112.
25. (b) Luppi, G.; Soffre, C.; Tomasini, C. Tetrahedron: Asymmetry 2004, 15, 1645-1650.
26. Cardillo, G.; Gentilucci, L.; De Matteis, V. J. Org. Chem. 2002, 67, 5957.
27. 2O. Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2005, 127, 18093.
28. Wu, C.; Lei, H.; Duan, Y. J. Am. Chem. Soc. 2005, 127, 13530 and references cited therein.
29. Samarium(II) diiodide was prepared according to a literature procedure. Girard, P.: Namy, J.-L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.