3-Aminopyrrolidines via ring rearrangement of 2-aminomethylazetidines. Synthesis of (-)-absouline

Organic Letters

Volumn 7, Issue 26, 2005, Pages 5861-5864

  Vargas Sanchez, Monica ^a   Couty, François ^a   Evano, Gwilherm ^a   Prim, Damien ^a   Marrot, Jérome ^a  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOULINE; ALKALOID; AZETIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AZETIDINES; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; PYRROLIDINES; STEREOISOMERISM;

EID: 30144437267     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052388e     Document Type: Article

References (34)

1. (a) Ikhiri, K.; Ahond, A.; Poupat, C.; Potier, P.; Pusset, J.; Sévenet, T. J. Nat. Prod. 1987, 50, 626.
2. (b) Neuner-Jehle, N.; Nesvadba, H.; Spiteller, G. Monatsh. Chem. 1965, 96, 321.
3. Barrett, J. F. Curr. Opin. Invest. Drugs 2000, 1, 45.
4. Iwanami, S.; Takashima, M.; Hirata, Y.; Hasegawa, O.; Usuda, S. J. Med. Chem. 1981, 24, 1224.
5. Wang, W. T.; Chen, Y.; Wang, S.; Gentles, R.; Sowin, T.; Kati, W.; Muchmore, S.; Giranda, V.; Stewart, K.; Sham, H.; Kempf, D.; Laver, W. G. J. Med. Chem. 2001, 44, 1192.
6. Corruble, A.; Valnot, J.-Y.; Maddaluno, J.; Duhamel, P. J. Org. Chem. 1998, 63, 8266.
7. Maddaluno, J.; Corruble, A.; Leroux, V.; Plé, G.; Duhamel, P. Tetrahedron: Asymmetry 1992, 3, 1239.
8. Lee, H.-S.; LePlae, P. R.; Porter, E. A.; Gellman, S. H. J. Org. Chem. 2001, 66, 3597.
9. Rosen, T.; Chu, D. T. W.; Lice, I. M.; Fernandes, P. B.; Shen, L.; Borodkin, S.; Pernet, A. G. J. Med. Chem. 1988, 31, 1586.
10. Andres, C. J.; Lee, P. H.; Nguyen, T. H.; Meyers, A. I. J. Org. Chem. 1995, 60, 3189.
11. (a) Couty, F.; Evano, G.; Prim, D. Mini-Rev. Org. Chem. 2004, 1, 133.
12. (b) Couty, F.; Durrat, F.; Evano, G.; Prim, D. Tetrahedron Lett. 2004, 45, 7525.
13. (c) Couty, F.; Durrat, F.; Evano, G. Synlett 2005, 1666.
14. Couty, F.; Evano, G.; Prim, D.; Marrot, J. Eur. J. Org. Chem. 2004, 3893.
15. Agami, C.; Couty, F.; Evano, G. Tetrahedron: Asymmetry 2002, 13, 297.
16. See Supporting Information for more details.
17. Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, Germany, 1991.
18. For recent examples of ring rearrangement starting from azetidines, see: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Salgado, N. R. J. Org. Chem. 1999, 64, 9596.
19. (b) Outurquin, F.; Pannecoucke, X.; Berthe, B.; Paulmier, C. Eur. J. Org. Chem. 2002, 1007.
20. (c) Couty, F.; Durrat, F.; Prim, D. Tetrahedron Lett. 2003, 44, 5209.
21. (d) Yoneda, R.; Sakamoto, Y.; Oketo, Y.; Harusawa, S.; Kurihara, T. Tetrahedron 1996, 52, 14563.
22. (e) O'Neil, I. A.; Potter, A. J. Chem. Commun. 1998, 1487.
23. (f) Martorell, A.; Inman, G. A.; Alper, H. J. Mol. Catal. A: Chem. 2003, 204, 91.
24. 2 is commonly used in Lewis acid-catalyzed ring openings of aziridines. See: (a) Bodenan, J.; Chanet-Ray, J.; Vessiere, R. Synthesis 1992, 288.
25. (b) Dauban, P.; Dodd, R. H. J. Org. Chem. 1997, 62, 4277.
26. (c) Cantrill, A. A.; Osborn, H. M. I.; Sweeney, J. Tetrahedron 1998, 54, 2181.
27. (d) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
28. (e) Xiong, C.; Wang, W.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 1399.
29. (f) Concellón, J. M.; Riego, E. J. Org. Chem. 2003, 68, 6407.
30. (g) Concellón, J. M.; Riego, E.; Suárez, R. J. Org. Chem. 2003, 68, 9242.
31. Christine, C.; Ikhiri, K.; Ahond, A.; Al Mourabit, A.; Poupat, C.; Potier, P. Tetrahedron 2000, 56, 1837.
32. Tang, T.; Ruan, Y. P.; Ye, J. L.; Huang, P.-Q. Synlett 2005, 231.
33. Couty, F.; Evano, G.; Vargas-Sanchez, M.; Bouzas, G. J. Org. Chem. 2005, 70, 9028.
34. For asymmetric synthesis of 1-aminopyrrolizidine, see: Giri, N.; Petrini, M.; Profeta, R. J. Org. Chem. 2004, 69, 7303.