A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C

Hiroyoshi Takamura, Takashi Abe, Naoki Nishiuma, Rie Fujiwara, Takahiko Tsukeshiba, Isao Kadota

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C was investigated. The first and second generation stereocontrolled syntheses of the LM ring fragment were achieved via spiroacetalization as a key step, respectively. The polyether framework of the HIJKLM ring fragment was constructed in a convergent manner by using intramolecular allylation, ring-closing metathesis, and stereoselective hydrogenation to form the 36-methyl substituent as the key transformations.

Original languageEnglish
Pages (from-to)2245-2260
Number of pages16
JournalTetrahedron
Volume68
Issue number10
DOIs
Publication statusPublished - Mar 11 2012

Keywords

  • Ciguatoxin CTX3C
  • Convergent synthesis
  • Intramolecular allylation
  • Polyether marine natural product

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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