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

研究成果: Article査読

44 被引用数 (Scopus)

抄録

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).

本文言語English
ページ(範囲)10949-10970
ページ数22
ジャーナルTetrahedron
55
36
DOI
出版ステータスPublished - 1999 9 3
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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