A concise route to two distinct E-ring structures of ciguatoxins

Masayuki Inoue, Masafumi Iwatsu, Shuji Yamashita, Masahiro Hirama

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Ciguatoxins, the causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers, and known to have more than 20 structurally distinct congeners. In this paper, we describe a new concise synthesis of the two E-ring structures, of different ring sizes, found in ciguatoxins.From the common oxepane intermediate, the seven-membered E-ring was prepared in three steps, and the eight-membered E-ring was synthesized in seven steps using ring expansion and olefin isomerization as key reactions.

Original languageEnglish
Pages (from-to)327-338
Number of pages12
JournalHeterocycles
Volume72
DOIs
Publication statusPublished - 2007 Apr 13

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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    Inoue, M., Iwatsu, M., Yamashita, S., & Hirama, M. (2007). A concise route to two distinct E-ring structures of ciguatoxins. Heterocycles, 72, 327-338. https://doi.org/10.3987/COM-06-S(K)16