A novel three-component butenolide synthesis

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2875-2878

  Beck, Barbara ^a   Magnin Lachaux, Marina ^a   Herdtweck, Eberhardt ^b   Dömling, Alexander ^a  

^a Biovertis AG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BUTENOLIDE; CYANIDE; DRUG DERIVATIVE; FURAN DERIVATIVE; GAMMA BUTYROLACTONE; GLYOXAL; IMMUNOSUPPRESSIVE AGENT;

ARTICLE; CHEMISTRY; SYNTHESIS;

4-BUTYROLACTONE; CYANIDES; FURANS; GLYOXAL; IMMUNOSUPPRESSIVE AGENTS;

EID: 0035817974     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016328u     Document Type: Article

References (40)

1. Barton, D. H. R. Aldrichimica Acta 1990, 23, 3.
2. Recent examples: (a) Semple, J. E.; Owens T. D.; Nguyen, K.; Levy, O. E. Org. Lett. 2000, 2, 2769-2772.
3. (b) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074-1076.
4. (c) Armstrong, R. W. J. Org. Chem. 1998, 63, 867-871.
5. (d) Nair, L. G.; Fraser-Reid, B.; Szardenings, A. K. Org. Lett. 2001, 3, 317.
6. (e) Heck, S.; Dömling, A. Synlett 2000, 424.
7. (f) Ballini, R.; Bosica, G.; Conforti, M. L.; Maggi, R.; Mazzacani, A.; Righi, P.; Sartori, G. Tetrahedron Lett. 2001, 57, 1395.
8. (g) Dumetsre, P.; El Kaim, L.; Gregoire, A. Chem. Commun. 1999, 775.
9. (h) Shaabani, A.; Yavari, I.; Teimouri, M. B.; Bazigir, A. Tetrahedron 2001, 57, 1375.
10. Scheffler, G.; Justus, M.; Vasella, A.; Wessel, H. P. Tetrahedron Lett. 1999, 40, 5845.
11. (j). Petasis, N. A.; Patel, Z. D. Tetrahedron Lett., 2000, 41, 9607.
12. Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
13. Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. 1997, 765.
14. Beck, B.; Hess, S.; Dömling, A. Biorg. Med. Chem. Lett. 2000, 10, 1701.
15. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1993, 32, 563.
16. Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709.
17. Review: Repke, K. R. H.; Megges, R.; Weiland, J.; Schön, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 282.
18. Zapf, S.; Anke, T.; Sterner, O. Acta Chem. Scand. 1995, 49, 233.
19. Scott, L. I.; Lamb, H. M. Drugs 1999, 3, 499.
20. For a review on butenolide synthesis, see: (a) Rao, Y. S. Chem. Rev. 1976, 76, 625. The reaction of α-acidic acetic acids (cyan acetic acid, arensulfonylacetic acids, 2-nitrophenylacetic acid) with glyoxals and isocyanides followed by Dieckmann-type condensations resulting in 5-aminoacyl-2(5H)-furanones has been reported:
21. (b) Bossio, R.; Marcaccim, S.; Pepino, R.; Torroba, T. Synthesis 1993, 783.
22. (c) Bossio, R.; Marcaccini, S.; Pepino, R. Liebigs Ann. Chem. 1994, 5, 527.
23. (d) Marcaccini, S.; Pepino, R.; Marcos, C. F.; Polo, C.; Torroba, T. J. Heterocyl. Chem. 2000, 37, 1501.
24. Passerini, M. Gazz. Chim. Ital. 1924, 54, 529.
25. Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624.
26. b). (a) Sheldrick G. M. SHELXS-86, University of Göttingen: Germany, 1997.
27. (b) Sheldrick G. M. SHELXL-97, University of Göttingen: Germany, 1997.
28. Coutrot, P.; Ghribi, A. Synthesis 1986, 661.
29. Formamide dehydration: (a) Ugi, I.; Meyr, R. Angew. Chem. 1958, 70, 702.
30. (b) Ugi, I.; Meyr, R. Chem. Ber. 1960, 93, 239. Hoffmann's carbylamine method:
31. (c) Weber, W. P.; Gokel, G. W.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1972, 11, 520. Meyer's method (AgCN):
32. (d) Meyer, E. J. Prakt. Chem. 1866, 147.
33. (e) Boullanger, P.; Descotes, G. Tetrahedron Lett 1976, 38, 4327. Gassman's merhod (epoxides, TMS-CN):
34. 3):
35. (g) Appel, R.; Kleistück, R.; Ziehn, K. D. Angew. Chem., Int. Ed. Engl. 1971, 10, 132.
36. 2, dioxan/water: Edlin, C. D.; Faulkner, S.; Parker, D.; Wilkinsom, M. P. J. Chem. Soc., Chem. Commun. 1996, 1249.
37. 2: Evans, W. E.; Carr, C. J.; Krantz, J. C. J. Am. Chem. Soc. 1938, 60, 1628.
38. (c) dmso, HBr: Ushami, K.; Isobe, M. Tetrahedron 1996, 37, 12061.
39. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
40. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.