A two-directional approach to pyrrolizidines: Total syntheses and biological evaluation of alkaloid cis-223B and (±)-xenovenine

Chemical Communications

Volumn 49, Issue 89, 2013, Pages 10507-10509

  Barthelme, Alexandre ^a   Richards, David ^a   Mellor, Ian R ^a   Stockman, Robert A ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; NEURONS; OXIDATION-REDUCTION; PATCH-CLAMP TECHNIQUES; PYRROLIZIDINE ALKALOIDS; RECEPTORS, CHOLINERGIC; STEREOISOMERISM;

PYRROLIZIDINE ALKALOID;

AMINATION; ANURA; ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; ELECTROPHYSIOLOGY; MELANOPHRYNISCUS STELZNERI; NONHUMAN; SOLENOPSIS; SOLENOPSIS XENOVENEUM; STEREOCHEMISTRY; SYNTHESIS;

EID: 84885581658     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc46800c     Document Type: Article

References (30)

1. M. Garraffo, T. F. Spande, J. W. Daly, A. Baldessari, E. G. Gros, J. Nat. Prod., 1993, 56, 357
2. R. Liddell, Nat. Prod. Rep., 1998, 15, 363-370
3. N. Asano, R. J. Nash, R. J. Molyneux, G. W. J. Fleet, Tetrahedron: Asymmetry, 2000, 11, 1645
4. G. King, J. Meinwald, Chem. Rev., 1996, 96, 1105-1122
5. B. Tursch, J. C. Braekman, D. Daloze, C. Hootele, D. Losman, R. Karlsson, J. M. Pasteels, Tetrahedron Lett., 1973, 201
6. B. Tursch, D. Daloze, J. C. Braekman, C. Hootele, J. M. Pasteels, Tetrahedron, 1975, 31, 1541
7. W. A. Ayer, L. M. Browne, Heterocycles, 1977, 7, 685
8. S. J. Roe, J.-C. Legeay, D. Robbins, P. Aggarwal, R. A. Stockman, Chem. Commun., 2009, 4399
9. A. F. Newton, S. J. Roe, J.-C. Legeay, P. Aggarwal, C. Gignoux, N. J. Birch, R. Nixon, M.-L. Alcaraz, R. A. Stockman, Org. Biomol. Chem., 2009, 7, 2274
10. W. Daly, T. F. Spande, H. M. Garraffo, J. Nat. Prod., 2005, 68, 1556
11. J.-C. Legeay, W. Lewis, R. A. Stockman, Chem. Commun., 2009, 2207
12. N. Toyooka, D. J. Zhou, H. Nemoto, Y. Tezuka, S. Kadota, N. R. Andriamaharavo, H. M. Garraffo, T. F. Spande, J. W. Daly, J. Org. Chem., 2009, 74, 6784
13. H. Jones, M. S. Blum, H. M. Fales, C. R. Thompson, J. Org. Chem., 1980, 45, 4778-4780
14. D. Lathbury, T. Gallagher, J. Chem. Soc., Chem. Commun., 1986, 1017
15. T. Jiang, T. Livinghouse, Org. Lett., 2010, 12, 4271
16. H. Takahata, H. Bandoh, T. Momose, J. Org. Chem., 1992, 57, 4401
17. V. M. Arredondo, S. Tian, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc., 1999, 121, 3633
18. X. K. Liu, X. Zheng, Y. P. Ruan, J. Ma, P. Q. Huang, Org. Biomol. Chem., 2012, 10, 1275
19. H. Jones, R. J. Highet, A. W. Don, M. S. Blum, J. Org. Chem., 1986, 51, 2712
20. S. Prakash, T. N. Pereira, P. E. B. Reilly, A. A. Seawright, Mutat. Res., 1999, 443, 53
21. I. Narberhaus, V. Zintgraf, S. Dobler, Chemoecology, 2005, 15, 121
22. H. Tsuneki, Y. You, N. Toyooka, S. Kagawa, S. Kobayashi, T. Sasaoka, H. Nemoto, I. Kimura, J. A. Dani, Mol. Pharmacol., 2004, 66, 1061
23. N. Toyooka, H. Tsuneki, S. Kobayashi, Z. Dejun, M. Kawasaki, I. Kimura, T. Sasaoka, H. Nemoto, Curr. Chem. Biol., 2007, 1, 97
24. X. Wang, H. Tsuneki, N. Urata, Y. Tezuka, T. Wada, T. Sasaoka, H. Sakai, R. A. Saporito, N. Toyooka, Eur. J. Org. Chem., 2012, 7082
25. T. Schmeller, A. El-Shazly, M. Wink, J. Chem. Ecol., 1997, 23, 399
26. H. Takahata, S. Takahashi, N. Azer, A. T. Eldefrawi, M. E. Eldefrawi, Bioorg. Med. Chem. Lett., 2000, 10, 1293
27. B. Badio, D. Ski, Y. Shin, K. D. Hutchinson, W. L. Padgett, J. W. Daly, Biochem. Pharmacol., 1996, 52, 933
28. T. Brior, I. R. Mellor, D. B. Tikhonov, I. Neagoe, Z. Shao, M. J. Brierley, K. Strømgaard, J. W. Jaroszewski, P. Krogsgaard-Larsen, P. N. R. Usherwood, Mol. Pharmacol., 2003, 64, 954
29. C. Gignoux, A. F. Newton, A. Barthelme, M.-L. Alcaraz, R. A. Stockman, Org. Biomol. Chem., 2012, 10, 67
30. D. Robbins, A. F. Newton, C. Gignoux, J.-C. Legeay, A. Sinclair, M. Rejzek, C. A. Laxon, S. K. Yalamanchili, W. Lewis, M. A. O'Connell, R. A. Stockman, Chem. Sci., 2011, 2, 2232