Stereoselective 6-exo radical cyclization using cis-Vinyl sulfoxide: Practical total synthesis of CTX3C

Shuji Yamashita, Yuuki Ishihara, Hiroyuki Morita, Junichi Uchiyama, Katsutoshi Takeuchi, Masayuki Inoue, Masahiro Hirama

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers. We report a highly stereoselective 6-exo radical cyclization/ring-closing olefin metathesis sequence to construct the syn/trans-fused polyether system. The new method was applied to the practical synthesis of ciguatoxin CTX3C.

Original languageEnglish
Pages (from-to)357-364
Number of pages8
JournalJournal of Natural Products
Volume74
Issue number3
DOIs
Publication statusPublished - 2011 Mar 25

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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    Yamashita, S., Ishihara, Y., Morita, H., Uchiyama, J., Takeuchi, K., Inoue, M., & Hirama, M. (2011). Stereoselective 6-exo radical cyclization using cis-Vinyl sulfoxide: Practical total synthesis of CTX3C. Journal of Natural Products, 74(3), 357-364. https://doi.org/10.1021/np100729d