Synthetic approach toward the structural elucidation of symbiodinolide: Stereodivergent synthesis and stereostructural revision of the C79-C104 fragment

Research output: Contribution to journalArticle

Abstract

Stereoselective synthesis of the proposed C79-C104 fragment of symbiodinolide, a polyol marine natural product, revealed that the stereochemistry of the C91-C99 carbon chain domain of this natural product needs to be reassigned. Next, stereodivergent synthesis of eight possible diastereomers corresponding to the C79-C97 and C94-C104 fragments resulted in the proposal of two candidate stereostructures, respectively. The synthesis of four candidate compounds of the C79-C104 fragment and comparison of their 13 C NMR data with those of the natural product allowed stereostructural revision of this fragment of symbiodinolide.

Original languageEnglish
Pages (from-to)474-477
Number of pages4
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume76
Issue number5
DOIs
Publication statusPublished - Jan 1 2018

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Biological Products
Stereochemistry
Carbon
Nuclear magnetic resonance
symbiodinolide

Keywords

  • Natural product
  • Polyol
  • Stereochemistry
  • Stereodivergent synthesis
  • Stereoselective synthesis
  • Structural elucidation
  • Symbiodinolide
  • Synthetic approach

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "Stereoselective synthesis of the proposed C79-C104 fragment of symbiodinolide, a polyol marine natural product, revealed that the stereochemistry of the C91-C99 carbon chain domain of this natural product needs to be reassigned. Next, stereodivergent synthesis of eight possible diastereomers corresponding to the C79-C97 and C94-C104 fragments resulted in the proposal of two candidate stereostructures, respectively. The synthesis of four candidate compounds of the C79-C104 fragment and comparison of their 13 C NMR data with those of the natural product allowed stereostructural revision of this fragment of symbiodinolide.",
keywords = "Natural product, Polyol, Stereochemistry, Stereodivergent synthesis, Stereoselective synthesis, Structural elucidation, Symbiodinolide, Synthetic approach",
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