Mirror image synthesis left ends of ciguatoxin and gambiertoxin 4b

Seijiro Hosokawa, Minoru Isobe

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87 Citations (Scopus)

Abstract

Three compounds related to the AB fragments of ciguatoxin and gambiertoxin 4b and two diastereomers (at the C-2 position) of the ABC fragment of ciguatoxin have been synthesized in enantiomeric form. The stereochemistry of the C-2 position was introduced selectively from the corresponding pentose derivative. Construction of the A ring with its side chain was completed by Nicholas type cyclization of an acetylene bis(cobalthexacarbonyl) complex followed by reductive decomplexation.

Original languageEnglish
Pages (from-to)37-48
Number of pages12
JournalJournal of Organic Chemistry
Volume64
Issue number1
DOIs
Publication statusPublished - 1999 Jan 8
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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