A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin

Masayuki Inoue, Makoto Sasaki, Kazuo Tachibana

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

A new strategy for the construction of the fused hexahydrooxonine ring system has been developed. The present synthesis involves an intramolecular reaction of γ-alkoxyallylsilane with acetal to form an O-linked oxacycle and a SmI2-mediated intramolecular Reformatsky reaction for constructing an oxonane ring as the key steps. Thermodynamic behavior of the trans-fused hexahydrooxonine ring was clarified for the first time and the conformational alternation was reproduced in the 6-9-6 tricyclic model compound 1 as was observed for that in the ciguatoxin molecule (ring F).

Original languageEnglish
Pages (from-to)10949-10970
Number of pages22
JournalTetrahedron
Volume55
Issue number36
DOIs
Publication statusPublished - 1999 Sep 3

Keywords

  • Conformation
  • Medium-ring heterocycles
  • Polyethers
  • Reformatsky reactions

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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