Highly diastereocontrolled synthesis of the C1-C25 domain of sanglifehrin A

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 3789-3792

  Duan, Maosheng ^a   Paquette, Leo A ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Aldol reaction; Enol borinate; Immunosuppressive agents; Peptide coupling; Vinyl iodide

Indexed keywords

SANGLIFEHRIN A;

ARTICLE; BINDING AFFINITY; DRUG ISOLATION; DRUG SYNTHESIS; PROTEIN DOMAIN; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0034697542     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00504-9     Document Type: Article

References (25)

1. (a) Fehr, T.; Oberer, L. Intern. Patent Appl. W097/02285, January 23, 1997.
2. (b) Fehr, T.; Oberer, L.; Quesniaux, R. V.; Sanglier, J.-J.; Schuler, W.; Sedrani, R. Intern. Patent Appl. W098/07743, March 3, 1998.
3. (a) Sanglier, J.-J.; Quesniaux, V.; Fehr, T.; Hofmann, H.; Mahnuke, M.; Memmert, K.; Schuler. W.; Zeknke, G.; Gschwind, L.; Maurer, C.; Schilling, W. J. Antibiot. 1999, 52, 466.
4. (b) Fehr, T.; Kallen, J.; Oberer, L.; Sanglier, J.-J.; Schilling, W. J. Antibiot. 1999, 52, 474.
5. Paquette, L. A.; Konetzki, I.; Duan, M. Tetrahedron Lett. 1999, 40, 7441.
6. (a) Bänteli, R.; Brun, I.; Hall, P.; Metteruich, R. Tetrahedron Lett. 1999, 40, 2109.
7. (b) Metternich, R.; Denni, D.; Thai, B.; Sedrani, R. J. Org. Chem. 1999, 64, 9632.
8. (a) Nicolaou, K. C.; Xu, J.; Murphy, F.; Barluenga, S.; Baudoin, O.; Wei, H.-x.; Gray, D. L. F.; Ohshima, T. Angew. Chem., Int. Ed. 1999, 38, 2447.
9. (b) Nicolaou, K. C.; Ohshima, T.; Murphy, F.; Barluenga, S.; Xu, J.; Winssinger, N. Chem. Commun. 1999, 809.
10. Rivero, R. A.; Greenlee, W. J. Tetrahedron Lett. 1991, 32, 2453.
11. Evans, D. A.; Ennis, M. D.; Le, T. J. Am. Chem. Soc. 1984, 106, 1154.
12. The TBS analog of 3 has been previously reported: Smith III, A. B.; Ott, G. R. J. Am. Chem. Soc. 1998, 120, 3935.
13. Roush, W. R. J. Am. Chem. Soc. 1980, 102, 1390.
14. Oppolzer, W.; Dupuis, D.; Poli, G.; Raynham, T. M.; Bernardinelli, G. Tetrahedron Lett. 1988, 29, 5885.
15. Evans, D. A.; Ng, H. P.; Clark, J. S.; Rieger, D. L. Tetrahedron 1992, 48, 2127.
16. Paterson, I.; Yeung, K.-S.; Watson, C.; Ward, R. A.; Wallace, P. A. Tetrahedron 1998, 54, 11935. The specific experimental details can be found on page 11 946.
17. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
18. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 287.
19. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 5583.
20. The Negishi conditions (Negishi, E.; Van Horn, D. E.; King, A. O.; Okukado, N. Synthesis 1979, 501) proved to be too harsh for 10 and its derivatives.
21. Evans, D. A.; Britton, T. C.; Ellman, J. H. Tetrahedron Lett. 1987, 28, 6141.
22. Nicolaou, K. C.; King, N. P.; Finlay, M. V. R.; He, Y.; Roschangar, F.; Vourloumis, D.; Vallberg, H.; Sarabia, F.; Ninkovic, S.; Hepworth, D. Bioorg. Med. Chem. 1999, 7, 665.
23. 4 in THF with methanol as a co-solvent resulted in reductive deiodination.
24. Prashad, M.; Har, P.; Kim, H.-Y.; Repic, O. Tetrahedron Lett. 1998, 39, 7067.
25. Albericio, F.; Kates, S. A.; Carpino, L. A. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Editor-in-chief; John Wiley: Chichester, 1995; Vol. 3, pp. 2028-2031.