An aza-Prins cyclization approach to functionalized indolizidines from 2-allylpyrrolidines

Organic Letters

Volumn 14, Issue 21, 2012, Pages 5574-5577

  Liu, Xiaoxi ^a   McCormack, Michael P ^a   Waters, Stephen P ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CATALYSIS; CYCLIZATION; INDOLIZIDINES; MOLECULAR STRUCTURE; PYRROLIDINES;

EID: 84868341739     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302693u     Document Type: Article

References (33)

1. Lourenco, A. M.; Maximo, P.; Ferreira, L. M.; Pereira, M. M. A. In Studies in Natural Products Chemistry: Bioactive Natural Products (Part H); Rahman, A., Ed.; Elsevier: Amsterdam, 2002; Vol. 27, pp 233-298.
2. Takahata, H.; Momose, T. In The Alkaloids, Chemistry and Pharmacology; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1993; Vol. 44, pp 228-256.
3. Lourenco, A. M.; Maximo, P.; Ferreira, L. M.; Perira, M. M. A. In Studies in Natural Products Chemistry; Pahman, A. U., Ed.; Elsevier: Amsterdam, 2002; Vol. 27, pp 233-298.
4. Qin, S.; Liang, J.; Guo, Y. Helv. Chim. Acta 2009, 92, 399-403
5. Liras, S.; Davoren, J. E.; Bordner, J. Org. Lett. 2001, 3, 703-706
6. Bentler, J. A.; Karbon, E. W.; Brubaker, A. N.; Malik, R.; Curtis, D. R.; Enna, S. J. J. Brain Res. 1985, 330, 135-140
7. Michael, J. P. Nat. Prod. Rep. 2004, 21, 625-649
8. Michael, J. P. Nat. Prod. Rep. 2007, 24, 191-222
9. Kamal, A.; Vangala, S. R. Tetrahedron 2011, 67, 1341-1347
10. McCormack, M. P.; Shalumova, T.; Tanski, J. M.; Waters, S. P. Org. Lett. 2010, 12, 3906-3909
11. Dobbs, A. P.; Guesne, S. J. J.; Parker, R. J.; Skidmore, J.; Stephenson, R. A.; Hursthouse, M. B. Org. Biomol. Chem. 2010, 8, 1064-1080
12. Ohmiya, S.; Higashiyama, K.; Otomasu, H.; Haginiwa, J.; Murakoshi, I. Phytochemistry 1981, 20, 1997-2001
13. Liu, J.; Hsung, R. P.; Peters, S. D. Org. Lett. 2004, 6, 3989-3992
14. Armstrong, A.; Bhonoah, Y.; Shanahan, S. E. J. Org. Chem. 2007, 72, 8019-8024
15. Overman, L. E.; Bell, K. L. J. Am. Chem. Soc. 1981, 103, 1851-1853
16. Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 1988, 110, 612-614
17. Lin, H.; Overman, L E.; Rabinowitz, M. H.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9073-9082
18. Nishimura, T.; Unni, A. K.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2011, 133, 418-419
19. Larsen, S. D.; Grieco, P. A.; Fobare, W. F. J. Am. Chem. Soc. 1986, 108, 3512-1513
20. Padwa, A.; Bur, S. K. Tetrahedron 2007, 63, 5341-5378
21. Esch, P. M.; de Boer, R. F.; Hiemstra, H.; Boska, I. M.; Speckamp, W. N. Tetrahedron 1991, 47, 4063-4076
22. Carballo, R. M.; Ramirez, M. A.; Rodriguez, M. L.; Martin, V. S.; Padron, J. I. Org. Lett. 2006, 8, 3837-3840
23. Subba Reddy, B. V.; Chaya, D. M.; Yadav, J. S.; Grée, R. Synthesis 2012, 44, 297-303
24. Smith, A. B.; Dae-Shik, K. J. Org. Chem. 2006, 71, 2547-2557
25. Sattely, E. S.; Cortez, G. A.; Moebius, D. C.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 8526-8533
26. Park, S. H.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621-2624
27. Manzoni, L.; Arosio, D.; Belvisi, L.; Bracci, A.; Colombo, M.; Invernizzi, D.; Scolastico, C. J. Org. Chem. 2005, 70, 4124-4132
28. For a limited, early example, see: Esch, P. M.; Boska, I. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1991, 47, 4039-4062
29. Lapointe, G.; Schenk, K.; Renaud, P. Chem.-Eur. J. 2011, 17, 3207-3212
30. Coldham, I.; Jana, S.; Watson, L.
31. Martin, N. G. Org. Biomol. Chem. 2009, 7, 1674-1679
32. Chou, S. P.; Chung, Y. C.; Chan, P. A.; Chiang, S. L.; Wu, C. J. J. Org. Chem. 2011, 76, 692-695
33. Hays, S. J.; Malone, T. C.; Johnson, G. J. Org. Chem. 1991, 56, 4084-4086