Cyclization of aminocyclopropanes in indole alkaloids synthesis

Synlett

Volumn , Issue 5, 2011, Pages 589-593

  De Simone, Filippo ^a   Waser, Jérôme ^a  

^a EPFL   (Switzerland)

Author keywords

alkaloids; aminocyclopropanes; cyclization; iminium; indoles

Indexed keywords

AMINOCYCLOPROPANE DERIVATIVE; ASPIDOSPERMINE; CYCLOPROPANE DERIVATIVE; DICHLOROMETHANE; INDOLE ALKALOID; LEWIS ACID; STRYCHNINE; UNCLASSIFIED DRUG; VINBLASTINE; VINCRISTINE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; DRUG STRUCTURE; ELECTROPHILICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; PHASE TRANSITION; STOICHIOMETRY;

EID: 79952454749     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259553     Document Type: Article

References (53)

1. Ma S M., In Handbook of Cyclization Reactions Wiley-VCH Weinheim 2009
2. Reissig H U., Zimmer R, Chem. Rev. 2003 103 1151
3. Gnad F, Reiser O, Chem. Rev. 2003 103 1603
4. Yu M, Pagenkopf B L., Tetrahedron 2005 61 321
5. Carson C A., Kerr M A., Chem. Soc. Rev. 2009 38 3051
6. De Simone F, Waser J, Synthesis 2009 3353
7. Lebold T P., Kerr M A., Pure Appl. Chem. 2010 82 1797
8. Stork G, Marx M, J. Am. Chem. Soc. 1969 91 2371
9. Stork G, Gregson M, J. Am. Chem. Soc. 1969 91 2373
10. Stork G, Grieco P A., J. Am. Chem. Soc. 1969 91 2407
11. Corey E J., Balanson R D., Tetrahedron Lett. 1973 3153
12. Danishefsky S, Acc. Chem. Res. 1979 12 66
13. Wenkert E, Alonso M E., Buckwalter B L., Chou K J., J. Am. Chem. Soc. 1977 99 4778
14. Wenkert E, Acc. Chem. Res. 1980 13 27
15. Reissig H U., Hirsch E, Angew. Chem., Int. Ed. Engl. 1980 19 813
16. Brückner C, Reissig H U., Angew. Chem., Int. Ed. Engl. 1985 24 588
17. For a few leading references, see:, Yu M, Pagenkopf B L., J. Am. Chem. Soc. 2003 125 8122
18. Yu M, Pagenkopf B L., Org. Lett. 2003 5 5099
19. Young I S., Kerr M A., Org. Lett. 2004 6 139
20. Young I S., Williams J L., Kerr M A., Org. Lett. 2005 7 953
21. Pohlhaus P D., Johnson J S., J. Org. Chem. 2005 70 1057
22. Parsons A T., Johnson J S., J. Am. Chem. Soc. 2009 131 14202
23. Parsons A T., Smith A G., Neel A J., Johnson J S., J. Am. Chem. Soc. 2010 132 9688
24. Piers E, In Comprehensive Organic Synthesis Vol. 5 Trost B M. Pergamon New York 1991 971
25. Nazarov I N., Zaretskaya I I., Izv. Akad. Nauk. SSSR. Ser. Khim. 1941 211
26. Habermas K L., Denmark S E., Jones T K., Org. React. (N. Y.) 1994 45 1
27. Jones T K., Denmark S E., Helv. Chim. Acta 1983 66 2377
28. Liang G X., Trauner D, J. Am. Chem. Soc. 2004 126 9544
29. Frontier A J., Collison C, Tetrahedron 2005 61 7577
30. Pellissier H, Tetrahedron 2005 61 6479
31. Tius M A., Eur. J. Org. Chem. 2005 2193
32. Nakanishi W, West F G., Curr. Opin. Drug Discovery Dev. 2009 12 732
33. Murphy W S., Wattanasin S, Tetrahedron Lett. 1980 21 1887
34. Murphy W S., Wattanasin S, J. Chem. Soc., Perkin Trans. 1 1981 2920
35. Murphy W S., Wattanasin S, J. Chem. Soc., Perkin Trans. 1 1982 1029
36. Tsuge O, Kanemasa S, Otsuka T, Suzuki T, Bull. Chem. Soc. Jpn. 1988 61 2897
37. De Simone F, Waser J, Chimia 2009 63 162
38. De Simone F, Andres J, Torosantucci R, Waser J, Org. Lett. 2009 11 1023
39. He W, Herrick I R., Atesin T A., Caruana P A., Kellenberger C A., Frontier A J., J. Am. Chem. Soc. 2008 130 1003
40. Yadav V K., Kumar N V., Chem. Commun. 2008 3774
41. The introduction of an ester group in position to the ketone also allows a further polarization of the cyclopropane and an extension of the scope: Saget, T.; De Simone, F.; Waser, J. unpublished results
42. Patil D V., Phun L H., France S, Org. Lett. 2010 12 5684
43. Wenkert E, Halls T D. J., Kwart L D., Magnusson G, Showalter H D. H., Tetrahedron 1981 37 4017
44. Wenkert E, Hudlicky T, J. Org. Chem. 1988 53 1953
45. Kaufman M D., Grieco P A., J. Org. Chem. 1994 59 7197
46. Grieco P A., Kaufman M D., J. Org. Chem. 1999 64 7586
47. De Simone F, Gertsch J, Waser J, Angew. Chem. Int. Ed. 2010 49 5767
48. Jackson A, Wilson N D. V., Gaskell A J., Joule J A., J. Chem. Soc. C 1969 2738
49. Diez A, Castells J, Forns P, Rubiralta M, Grierson D S., Husson H P., Solans X, Fontbardia M, Tetrahedron 1994 50 6585
50. Forns P, Diez A, Rubiralta M, Solans X, FontBardia M, Tetrahedron 1996 52 3563
51. Amat M, Perez M, Llor N, Escolano C, Luque F J., Molins E, Bosch J, J. Org. Chem. 2004 69 8681
52. Forns P, Diez A, Rubiralta M, J. Org. Chem. 1996 61 7882
53. Cutri S, Diez A, Bonin M, Micouin L, Husson H P., Org. Lett. 2005 7 1911