Issue 1, 2014

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

Abstract

The stereocontrolled synthesis of a racemic carboxylic acid of crambescin B, a marine alkaloid, is described. The synthesis features two highly stereoselective reactions: (i) palladium-catalyzed hydroxymethylation of an alkynyl aziridine having an N-guanidino group and (ii) cascade bromocyclization providing a spiro-hemiaminal structure. The cell-based colorimetric assay showed that the synthesized carboxylic acid exhibited a potent inhibitory activity on voltage-gated sodium channels.

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

Supplementary files

Additions and corrections

Article information

Article type
Communication
Submitted
08 Oct 2013
Accepted
30 Oct 2013
First published
30 Oct 2013

Org. Biomol. Chem., 2014,12, 53-56

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

A. Nakazaki, Y. Ishikawa, Y. Sawayama, M. Yotsu-Yamashita and T. Nishikawa, Org. Biomol. Chem., 2014, 12, 53 DOI: 10.1039/C3OB42017E

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