Practical route to the left wing of CTX1B and total syntheses of CTX1B and 54-deoxyCTX1B

Shuji Yamashita, Katsutoshi Takeuchi, Takuya Koyama, Masayuki Inoue, Yujiro Hayashi, Masahiro Hirama

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Ciguatoxins, the principal causative agents of ciguatera seafood poisoning, are extremely large polycyclic ethers. We report herein a reliable route for constructing the left wing of CTX1B, which possesses the acid/base/oxidantsensitive bisallylic ether moiety, by a 6-exo radical cyclization/ring-closing metathesis strategy. This new route enabled us to achieve the second-generation total synthesis of CTX1B and the first synthesis of 54-deoxyCTX1B.

Original languageEnglish
Pages (from-to)2621-2628
Number of pages8
JournalChemistry - A European Journal
Volume21
Issue number6
DOIs
Publication statusPublished - 2015 Feb 2

Keywords

  • Ciguatoxin
  • Polycyclic ether
  • Radical reaction
  • Ring-closing metathesis
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Practical route to the left wing of CTX1B and total syntheses of CTX1B and 54-deoxyCTX1B'. Together they form a unique fingerprint.

  • Cite this