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

11 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

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Hydrogenation
Hand
Allylation
Polyethers
ciguatoxin 3C

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C. / Takamura, Hiroyoshi; Abe, Takashi; Nishiuma, Naoki; Fujiwara, Rie; Tsukeshiba, Takahiko; Kadota, Isao.

In: Tetrahedron, Vol. 68, No. 10, 11.03.2012, p. 2245-2260.

Research output: Contribution to journalArticle

Takamura, Hiroyoshi ; Abe, Takashi ; Nishiuma, Naoki ; Fujiwara, Rie ; Tsukeshiba, Takahiko ; Kadota, Isao. / A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C. In: Tetrahedron. 2012 ; Vol. 68, No. 10. pp. 2245-2260.
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