Asymmetric synthesis of highly substituted azapolycyclic compounds via 2-alkenyl sulfoximines: Potential scaffolds for peptide mimetics

Journal of the American Chemical Society

Volumn 128, Issue 12, 2006, Pages 4023-4034

  Reggelin, Michael ^a   Junker, Bernd ^a,b   Heinrich, Timo ^a,c   Slavik, Stefan ^a   Bühle, Philipp ^a,c  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

^c MERCK KGAA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; IODINE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AZAHETEROCYCLES; CYCLIZATION; NON-PEPTIDE MIMETICS;

POLYCYCLIC AROMATIC HYDROCARBONS;

ALDEHYDE; ALLYL ALCOHOL; HETEROCYCLIC COMPOUND; IMINE; LEAD; PEPTIDE; POLYCYCLIC HYDROCARBON; SAMARIUM; SAMARIUM IODIDE; SULFOXIMINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CONFORMATION; CYCLIZATION; ENANTIOMER; PROTEIN STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS;

ALDEHYDES; ALKENES; BIOMIMETIC MATERIALS; METHIONINE; MODELS, MOLECULAR; PEPTIDES; PIPERIDINES; POLYCYCLIC COMPOUNDS; PYRROLIDINES; STEREOISOMERISM;

EID: 33645452024     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja057012a     Document Type: Article

References (49)

1. Bridging the gap between bioactive peptides and nonpeptides: some perspectives in design; Farmer, P. S., Ed.; Academic Press: New York, 1980; Vol. 11, p 119.
2. Ripka, A. S.; Rich, D. H, Curr. Opin. Chem. Biol. 1998, 2, 441.
3. Belanger, P. C.; Dufresne, C. Can. J. Chem. 1986, 64, 1514.
4. Snider, R. M.; Constantine, J. W.; Lowe, J. A., III; Longo, K. P.; Lebel, W. S.; Woody, H. A.; Drozda, S. E.; Desai, M. C.; Vinick, F. J.; Spencer, R. W.; Hess, H.-J. Science 1991, 251, 435.
5. McLean, S.; Ganong, A. H.; Seeger, T. F.; Bryce, D. K.; Pratt, K. G.; Reynolds, L. S.; Siok, C. J.; Lowe, J. A., III; Heym, J. Science 1991, 251, 437.
6. Lam, P. Y. S.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N.; Ru, Y.; Bacheler, L. T.; Meek, O. M. J.; Rayner, M. M. Science 1994, 263, 380.
7. Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Salvino, J.; Leahy, E. M.; Sprengeler, P. A.; Furst, G.; Smith, A. B., III; Strader, C. D.; Cascieri, M. A.; Candelore, M. R.; Donaldson, C.; Vale, W.; Maechler, L. J. Am. Chem. Soc. 1992, 114, 9217.
8. Guller, R.; Binggeli, A.; Breu, V.; Bur, D.; Fischli, W.; Hirth, G.; Jenny, C.; Kansy, M.; Montavon, F.; Muller, M.; Oefner, C.; Stadler, H.; Vieira, E.; Wilhelm, M.; Wostl, W.; Marki, H. P. Bioorg. Med. Chem. Lett. 1999, 9, 1403.
9. Vieira, E.; Binggeli, A.; Breu, V.; Bur, D.; Fischli, W.; Guller, R.; Hirth, G.; Marki, H. P.; Muller, M.; Oefner, C.; Scalone, M.; Stadler, H.; Wilhelm, M.; Wostl, W. Bioorg. Med. Chem. Lett. 1999, 9, 1397.
10. Oefner, C.; Binggeli, A.; Breu, V.; Bur, D.; Clozel, J. P.; D'Arcy, A.; Dorn, A.; Fischli, W.; Gruninger, F.; Guller, R.; Hirth, G.; Marki, H. P.; Mathews, S.; Muller, M.; Ridley, R. G.; Stadler, H.; Vieira, E.; Wilhelm, M.; Winkler, F. K.; Wostl, W. Chem. Biol. 1999, 6, 127.
11. Bursavich, M. G.; Rich, D. H. J. Med. Chem. 2002, 45, 541.
12. Fletcher, M. D.; Campbell, M. M. Chem. Rev. 1998, 98, 763.
13. Muller, G.; Hessler, G.; Decornez, H. Y. Angew. Chem., Int. Ed. 2000, 39, 894.
14. Hruby, V. J. Life Sci. 1982, 31, 189.
15. Richardson, J. S. Adv. Protein Chem. 1981, 34, 167.
16. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1.
17. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467.
18. Reggelin, M.; Weinberger, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 444.
19. For excellent related work on allylic sulfoximines see: (a) Gais, H. J.; Bruns, P. R.; Raabe, G.; Hainz, R.; Schleusner, M.; Runsink, J.; Babu, G. S. J. Am. Chem. Soc. 2005, 127, 6617.
20. (b) Gais, H.-J.; Babu, G. S.; Guenter, M.; Das, P. Eur. J. Org. Chem. 2004, 1464.
21. Gais, H.-J.; Hainz, R.; Muller, H.; Bruns, P. R.; Giesen, N.; Raabe, G.; Runsink, J.; Nienstedt, S.; Decker, J.; Schleusner, M.; Hachtel, J.; Loo, R.; Woo, C.-W.; Das, P. Eur. J. Org. Chem. 2000, 3973.
22. Gais, H.-J.; Mueller, H.; Decker, J.; Hainz, R. Tetrahedron Lett. 1995, 36, 7433.
23. Reggelin, M.; Gerlach, M.; Vogt, M. Eur. J. Org. Chem. 1999, 1011.
24. Reggelin, M.; Heinrich, T. Angew. Chem., Int. Ed. 1998, 37, 2883.
25. Reggelin, M.; Weinberger, H.; Heinrich, T. Liebigs Ann. Recl. 1997, 1881.
26. Reggelin, M.; Weinberger, H.; Gerlach, M.; Welcker, R. J. Am. Chem. Soc. 1996, 118, 4765.
27. Reggelin, M.; Weinberger, H. Tetrahedron Lett. 1992, 33, 6959.
28. Reggelin, M.; Welcker, R. Tetrahedron Lett. 1995, 36, 5885.
29. Reggelin, M.; Junker, B. Chem.-Eur. J. 2001, 7, 1232.
30. Schroeder, E. Liebigs Ann. 1963, 670, 127.
31. Myers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359.
32. We thank Merck (Darmstadt) for a generous gift of ester 32.
33. Iwao, M.; Kuraishi, T. Org. Synt. 1996, 73, 85.
34. Meyers, A. I.; Milot, G. J. Org. Chem. 1993, 58, 6538.
35. Iwao, M.; Kuraishi, T. Heterocycles 1992, 34, 1031.
36. Bats, J. W.; Heinrich, T.; Reggelin, M. Acta Crystallogr. 1998, C54, IUC9800033.
37. Bolte, M. Acta Crystallogr. 1997, C53, IUC9700028.
38. Bats, J. W.; Heinrich, T.; Reggelin, M. Acta Crystallogr. 1998, C54, IUC9800039.
39. Bats, J. W.; Heinrich, T.; Reggelin, M. Acta Crystallogr. 1998, C54, IUC9800038.
40. Heinrich, T.; Reggelin, M.; Bats, J. W. Acta Crystallogr. 1999, C55, IUC9900131.
41. Reggelin, M.; Slavik, S., unpublished results.
42. Takasaki, M.; Konoshima, T.; Kozuka, M.; Haruna, M.; Ito, K.; Shingu, T. Chem. Pharm. Bull. 1994, 42, 2591.
43. Routier, S.; Sauge, L.; Ayerbe, N.; Coudert, G.; Merour, J. Y. Tetrahedron Lett. 2002, 43, 589.
44. Desai, M. C.; Lefkowitz, S. L.; Thaideio, P. F.; Longo, K. P.; Snider, R. M. J. Med. Chem. 1992, 35, 4911.
45. Lowe, J. A., III; Drodzda, S. E.; Snider, R. M.; Longo, K. P.; Zorn, S. H.; Morrone, J.; Jackson, E. R.; McLean, S.; Bryce, D. K.; Bordner, J.; Nagahisa, A.; Kanal Y.; Suga, O.; Tsuchiya, M. J. Med. Chem. 1992, 35, 2591.
46. Appell, K. C.; Fragale, B. J.; Loscig, J.; Singh, S.; Tomczuk, B. E. Am. Soc. Pharmacol. Experim. Therapeut. 1992, 772.
47. Harrison, T.; Williams, B. J.; Swain, C. J.; Ball, R. G. Bioorg. Med. Chem. Lett. 1994, 4, 2545.
48. Craig, D. A. Trends Pharmacol. Sci. 1993, 14, 89.
49. We thank Dr. R. Brückner (Solvay Pharmaceuticals, Hannover, Germany) for providing us with the biological data for 85 and 86.