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

Atsuo Nakazaki, Yuki Ishikawa, Yusuke Sawayama, Mari Yotsu-Yamashita, Toshio Nishikawa

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)53-56
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number1
DOIs
Publication statusPublished - 2014 Jan 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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