Synthesis of crambescin B carboxylic acid, a potent inhibitor of voltage-gated sodium channels

Organic and Biomolecular Chemistry

Volumn 12, Issue 1, 2014, Pages 53-56

  Nakazaki, Atsuo ^a   Ishikawa, Yuki ^a   Sawayama, Yusuke ^a   Yotsu Yamashita, Mari ^b   Nishikawa, Toshio ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS;

COLORIMETRIC ASSAYS; HYDROXYMETHYLATION; INHIBITORY ACTIVITY; PALLADIUM-CATALYZED; POTENT INHIBITOR; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE REACTIONS; SYNTHESIS FEATURES;

IONIC LIQUIDS;

CARBOXYLIC ACID; CRAMBESCIN B; PYRIMIDINE DERIVATIVE; SPIRO COMPOUND; VOLTAGE GATED SODIUM CHANNEL;

ARTICLE; CHEMISTRY; COLORIMETRY; CONFORMATION; METABOLISM; STEREOISOMERISM; SYNTHESIS;

CARBOXYLIC ACIDS; COLORIMETRY; MOLECULAR CONFORMATION; PYRIMIDINES; SPIRO COMPOUNDS; STEREOISOMERISM; VOLTAGE-GATED SODIUM CHANNELS;

EID: 84889011559     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c3ob42017e     Document Type: Article

References (23)

1. R. G. S. Berlinck A. E. Trindade-Silva M. F. C. Santos Nat. Prod. Rep. 2012 29 1382 1406
2. T. Narahashi J. Toxicol., Toxin Rev. 2001 20 67 84
3. T. Narahashi Proc. Jpn. Acad., Ser. B 2008 84 147 154
4. L. E. Llewellyn Nat. Prod. Rep. 2006 23 200 222
5. M. Adachi T. Imazu M. Isobe T. Nishikawa J. Org. Chem. 2013 78 1699 1705
6. T. Nishikawa M. Isobe Chem. Rec. 2013 13 286 302
7. R. G. S. Berlinck J. C. Braekman D. Daloze K. Hallenga R. Ottinger I. Bruno R. Riccio Tetrahedron Lett. 1990 31 6531 6534
8. E. A. Jares-Erijman A. A. Ingrum F. Sun K. L. Rinehart J. Nat. Prod. 1993 56 2186 2188
9. S. Bondu G. Genta-Jouve M. Leiròs C. Vale J. Guigonis L. M. Botana O. P. Thomas RSC Adv. 2012 2 2828 2835
10. B. B. Snider Z. Shi J. Org. Chem. 1992 57 2526 2528
11. B. B. Snider Z. Shi J. Org. Chem. 1993 58 3828 3839
12. Y. Sawayama T. Nishikawa Synlett 2011 651 654
13. Y. Sawayama T. Nishikawa Angew. Chem., Int. Ed. 2011 50 7176 7178
14. Y. Sawayama T. Nishikawa J. Synth. Org. Chem., Jpn. 2012 70 1178 1186
15. H. Ohno H. Hamaguchi T. Tanaka Org. Lett. 2000 2 2161 2163
16. H. Ohno H. Hamaguchi T. Tanaka J. Org. Chem. 2001 66 1867 1875
17. J. Inuki A. Iwata S. Oishi N. Fujii H. Ohno J. Org. Chem. 2011 76 2072 2083
18. T. Katsuki, in Catalytic Asymmetric Synthesis, ed., I. Ojima, VCH, New York, 2000, ch. 6B
19. O. A. Wong Y. Shi Chem. Rev. 2008 108 3958 3987
20. H. Pellissier Tetrahedron 2010 66 1509 1555
21. Y. Ittah Y. Sasson I. Shahak S. Tsaroom J. Blum J. Org. Chem. 1978 43 4271 4273
22. M. Yotsu-Yamashita D. Urabe M. Asai T. Nishikawa M. Isobe Toxicon 2003 42 557 560
23. V. Martín C. Vale S. Bondu O. P. Thomas M. R. Vieytes L. M. Botana Chem. Res. Toxicol. 2013 26 169 178