Total synthesis of ciguatoxin and 51-hydroxyCTX3C

Masayuki Inoue, Keisuke Miyazaki, Yuuki Ishihara, Atsushi Tatami, Yuyu Ohnuma, Yuuya Kawada, Kazuo Komano, Shuji Yamashita, Nayoung Lee, Masahiro Hirama

Research output: Contribution to journalArticlepeer-review

75 Citations (Scopus)

Abstract

Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers with the 13 ether rings ranging from five- to nine-membered. In this paper, we describe the total synthesis of the two most toxic members of the ciguatoxin family, ciguatoxin 1 and 51-hydroxyCTX3C 2, based on a unified synthetic strategy. The key features in our syntheses were (i) direct construction of the O,S-acetal from the corresponding left and right wing fragments (3, 4, 14); (ii) stereo- and chemoselective radical reaction of the α-oxyradical with pentafluorophenyl acrylate to achieve cyclization of the seven-membered G-ring; (iii) ring-closing metathesis reaction to build the nine-membered F-ring; and (iv) an efficient protective group strategy using the oxidatively removable 2-naphthylmethyl groups.

Original languageEnglish
Pages (from-to)9352-9354
Number of pages3
JournalJournal of the American Chemical Society
Volume128
Issue number29
DOIs
Publication statusPublished - 2006 Jul 26

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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