A New Synthetic Route to the Skeleton of Saxitoxin, a Naturally Occurring Blocker of Voltage-Gated Sodium Channels

• Sawayama Yusuke

• Nishikawa Toshio

  Department of Applied Biological Sciences, Graduate School of Bioagricultural Sciences, Nagoya University

Abstract

Saxitoxin is as potent and specific blocker of voltage-gated sodium channels as tetrodotoxin. This unique biological activity has established the importance of these two small natural products in neurophysiological experiments. In order to find new blockers of the voltage-gated sodium channels, an efficient synthetic route to the skeleton of saxitoxin was developed. This new synthetic route is based on two key reactions (i) cascade cyclization of a guanidino-acetylene initiated by the bromocation (Br⁺) and (ii) transformation of the geminal-dibromomethylene moiety to enol acetate, and culminated in the total synthesis of decarbamoyl-α-saxitoxinol, a naturally-occurring analog of saxitoxin.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 70 (11), 1178-1186, 2012

  The Society of Synthetic Organic Chemistry, Japan

Details

• CRID: 1390282680316013312
• NII Article ID: 10031131197
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.70.1178
• COI: 1:CAS:528:DC%2BC38XhslCjt7bN
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 024087969
• Web Site: http://id.ndl.go.jp/bib/024087969
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024087969
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/70/11/70_1178/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed