An Ireland-Claisen rearrangement/RCM based approach for the construction of the EF-ring of ciguatoxin 3C

Keisuke Nogoshi, Daisuke Domon, Kenshu Fujiwara, Natsumi Kawamura, Ryo Katoono, Hidetoshi Kawai, Takanori Suzuki

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The EF-ring of ciguatoxin 3C, a marine toxin from the dinoflagellate Gambierdiscus toxicus, was stereoselectively synthesized by iterative use of a cyclic ether formation process based on chirality-transferring Ireland-Claisen rearrangement and ring-closing olefin metathesis.

Original languageEnglish
Pages (from-to)676-680
Number of pages5
JournalTetrahedron Letters
Volume54
Issue number7
DOIs
Publication statusPublished - 13 Feb 2013

Keywords

  • Fused cyclic ethers
  • Ireland-Claisen rearrangement
  • Natural product synthesis
  • Ring closing olefin metathesis
  • Stereoselective synthesis

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