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Ring-Closing Metathesis in Carbohydrate Annulation.

David J Holt1, William D Barker1, Paul R Jenkins1

  • 1Department of Chemistry, Leicester University, Leicester LE1 7RH (UK), Fax: (+44) 116-252-3789.

Angewandte Chemie (International Ed. in English)
|May 2, 2018
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Summary
This summary is machine-generated.

Ring-closing metathesis enables the formation of eight-membered rings from glucose derivatives. This method also allows for the preparation of enantiomerically pure tricyclic spiro compounds.

Keywords:
AnnulationCarbohydratesHomogeneous catalysisMetathesisRuthenium

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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Synthetic Chemistry

Background:

  • Glucose derivatives are versatile starting materials in organic synthesis.
  • Ring-closing metathesis is a powerful tool for forming carbon-carbon double bonds and cyclic structures.

Purpose of the Study:

  • To explore the application of ring-closing metathesis in the synthesis of novel carbohydrate-based cyclic compounds.
  • To investigate the formation of medium-sized rings (eight-membered) from glucose derivatives.
  • To prepare enantiomerically pure tricyclic spiro compounds.

Main Methods:

  • Ring-closing metathesis reaction of specifically designed glucose derivatives.
  • Use of ruthenium-based catalysts for the metathesis reaction.
  • Purification and characterization of the resulting cyclic products.

Main Results:

  • Successful synthesis of eight-membered rings from glucose derivatives.
  • Demonstration of the formation of enantiomerically pure tricyclic spiro compounds.
  • The developed method provides access to complex cyclic structures from readily available carbohydrate precursors.

Conclusions:

  • Ring-closing metathesis is an effective strategy for constructing medium-sized rings and complex polycyclic systems from glucose.
  • This approach offers a route to novel carbohydrate scaffolds with potential applications in medicinal chemistry and materials science.