Efficient synthesis of (±)-horsfiline through the MgI2-catalyzed ring- expansion reaction of a spiro[cyclopropane-1,3'-indol]-2'-one

Helvetica Chimica Acta

Volumn 83, Issue 6, 2000, Pages 1175-1181

  Fischer, Christian ^a   Meyers, Christiane ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYCLOPROPANE DERIVATIVE; HORSFILINE; INDOLE DERIVATIVE; MAGNESIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MEDICINAL PLANT; REACTION ANALYSIS;

EID: 0034100070     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20000607)83:6<1175::AID-HLCA1175>3.0.CO;2-D     Document Type: Article

References (37)

1. 'The Alkaloids: Chemistry and Biology', Ed. G. A. Cordell, Academic, San Diego, 1998, Vol. 51.
2. a) J. Leclereq, M.-C. De Pauw-Gillet, R. Bassleer, L. Angenot, J. Ethnopharmacol. 1986, 15, 305;
3. b) P. L. Dupont, J. Lamotte-Brasseur, O. Dideberg, H. Campsteyn, M. Vermeire, L. Angenot, Acta. Crystallogr., Sect. B. 1977, 33, 1801.
4. a) A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6477;
5. b) T. Matsuura, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6500.
6. a) T. Fukuyama, G. Liu, J. Am. Chem. Soc. 1996, 118, 7426;
7. b) M. E. Kuehne, T. Wang, P. J. Seaton, J. Org. Chem. 1996, 61, 6001;
8. c) T. D. Cushing, J. F. Sanz-Cervera, R. M. Williams, J. Am. Chem. Soc. 1996, 118, 557;
9. d) S. Atarashi, J.-K. Choi, D.-C. Ha, D. J. Hart, D. Kuzmich, C.-S. Lee, S. Ramesh, S. C. Wu, J. Am. Chem. Soc. 1997, 119, 6226;
10. e) T. Gan, R. Liu, P. Yu, S. Zhao, J. M. Cook, J. Org. Chem. 1997, 62, 9298;
11. f) S. Kozmin, V. H. Rawal, J. Am. Chem. Soc. 1998, 120, 13523;
12. g) M. E. Kuehne, F. Xu, J. Org. Chem. 1998, 63, 9434.
13. a) S. D. Edmondson, S. J. Danishefsky, Angew. Chem., Int. Ed. 1998, 37, 1138;
14. b) S. Edmondson, S. J. Danishefsky, L. Sepp-Lorenzino, N. Rosen, J. Am. Chem. Soc. 1999, 121, 2147.
15. a) J. Du Bois, C. S. Tomooka, J. Hong, E. M. Carreira, Acc. Chem. Res. 1997, 30, 364;
16. b) M. R. Mish, F. M. Guerra, E. M. Carreira, J. Am. Chem. Soc. 1997, 119, 8379;
17. c) G. A. Whitlock, E. M. Carreira, J. Org. Chem. 1997, 62, 7916;
18. d) J. Du Bois, C. S. Tomooka, J. Hong, E. M. Carreira, J. Am. Chem. Soc. 1997, 119, 3179;
19. e) J. Du Bois, C. S. Tomooka, J. Hong, E. M. Carreira, M. W. Day, Angew. Chem., Int. Ed. 1997, 36, 1645;
20. f) D. E. Frantz, R. Fässler, E. M. Carreira, J. Am. Chem. Soc. 1999, 121, 11245.
21. P. B. Alper, C. Meyers, A. Lerchner, D. R. Siegel, E. M. Carreira, Angew. Chem. Int. Ed. 1999, 38, 3186.
22. E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330.
23. A. Jossang, P. Jossang, H. A. Hadi, T. Sevenet, B. Bodo, J. Org. Chem. 1991, 56, 6527.
24. K. Jones, J. Wilkinson, J. Chem. Soc., Chem. Commun. 1992, 1767.
25. S.-I. Bascop, J. Sapi, J.-Y. Laronze, J. Lévy, Heterocycles 1994, 38, 725.
26. C. Pellegrini, C. Strässler, M. Weber, H.-J. Borschberg, Tetrahedron: Asymmetry 1994, 5, 1979.
27. G. Palmisano, R. Annunziata, G. Papeo, M. Sisti, Tetrahedron: Asymmetry 1996, 7, 1.
28. G. Lakshmaiah, T. Kawabata, M. Shang, K. Fuji, J. Org. Chem. 1999, 64, 1699.
29. a) E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797;
30. b) J. E. Saxton, Nat. Prod. Rep. 1997, 559.
31. J. P. Kutney, in 'The Synthesis of Indole Alkaloids', Ed. J. ApSimon, John Wiley & Sons, New York, 1977; Vol. 3, p. 273.
32. a) H. N. Wong, M.-Y. Hon. C.-W. Tse, Y-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165;
33. b) S. Danishefsky, Acc. Chem. Res. 1979, 12, 66.
34. a) A. B. Smith III, R. M. Scarborough Jr., Tetrahedron Lett. 1978, 1649;
35. b) L. Bagnell, A. Meisters, T. Mole, Aust. J. Chem. 1975, 28, 821.
36. H. Bibas, R. Koch, C. Wentrup, J. Org. Chem. 1998, 63, 2619.
37. Du Pont de Nemours & Co., US Pat. 2729679, 1951.