Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C

Megumi Maruyama, Masayuki Inoue, Tohru Oishi, Hiroki Oguri, Yoshihiro Ogasawara, Yumi Shindo, Masahiro Hirama

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Abstract

Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen 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 ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis.

Original languageEnglish
Pages (from-to)1835-1851
Number of pages17
JournalTetrahedron
Volume58
Issue number10
DOIs
Publication statusPublished - Mar 4 2002
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Maruyama, M., Inoue, M., Oishi, T., Oguri, H., Ogasawara, Y., Shindo, Y., & Hirama, M. (2002). Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C. Tetrahedron, 58(10), 1835-1851. https://doi.org/10.1016/S0040-4020(02)00041-8