A convergent synthesis of the decacyclic ciguatoxin model containing the F-M ring framework

Masayuki Inoue, Makoto Sasaki, Kazuo Tachibana

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56 Citations (Scopus)

Abstract

A highly convergent synthesis of the decacyclic ciguatoxin model 2, which contains the F-M ring framework of the natural product, has been achieved through the assembly of pentacyclic oxonane 4 and JKLM ring fragment 5. The two key steps in the synthesis of the former compound are (i) a Lewis acid-mediated intramolecular reaction of a γ-alkoxyallylsilane with an acetal group to form an O-linked oxacycle and (ii) a SmI2-mediated intramolecular Reformatsky reaction leading to construction of the annelated oxonane ring system. Preliminary biological investigations revealed that model compound 2 did not inhibit the binding of tritium-labeled dihydrobrevetoxin B to voltage-sensitive sodium channels at micromolar concentrations.

Original languageEnglish
Pages (from-to)9416-9429
Number of pages14
JournalJournal of Organic Chemistry
Volume64
Issue number26
DOIs
Publication statusPublished - 1999 Dec 24
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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