Convergent synthesis of the HIJKLM ring fragment of ciguatoxin CTX3C

Hisatoshi Uehara, Tohru Oishi, Masayuki Inoue, Mitsuru Shoji, Yoko Nagumo, Masashi Kosaka, Jean Yves Le Brazidec, Masahiro Hirama

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative agents of ciguatera food poisoning. The structure of CTX3C spans more than 3nm and is characterized by 13 ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the HIJKLM ring fragment and present a new carbonyl olefination protocol to cyclize the J ring using low-valent titanium.

Original languageEnglish
Pages (from-to)6493-6512
Number of pages20
JournalTetrahedron
Volume58
Issue number32
DOIs
Publication statusPublished - 2002 Aug 5

Keywords

  • CTX3C
  • Ciguatoxin
  • Intramolecular carbonyl olefination
  • Low-valent titanium complex
  • Polyether
  • Ring-closing metathesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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