Synthetic studies on ciguatoxin: A convergent strategy for construction of the F-M ring framework

Masayuki Inoue, Makoto Sasaki, Kazuo Tachibana

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

Exceptional neurotoxicity is associated with ciguatoxin. The ciguatoxin mimic 1, which contains the F-M framework of the natural product, has been prepared through a convergent synthesis. The two key steps were a Lewis acid mediated intramolecular reaction of a γ-alkoxyallylsilane with an acetal group and an SmI2-mediated intramolecular Reformatsky reaction that permitted construction of the annelated hexahydrooxonin ring system.

Original languageEnglish
Pages (from-to)965-969
Number of pages5
JournalAngewandte Chemie - International Edition
Volume37
Issue number7
DOIs
Publication statusPublished - 1998

Keywords

  • Ciguatoxin
  • Cyclizations
  • Natural products
  • Polyethers
  • Synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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