Synthetic Strategies for Converting Carbohydrates into Carbocycles by the Use of Olefin Metathesis

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Abstract

This microreview covers recent advances in the use of ring-closing metathesis for the synthesis of carbocycles from carbohydrates. Various strategies for the synthesis of a,w-dienes from carbohydrates are presented, which give rise to a large variety of dienes with different stereochemistry, protecting groups and substituents. Subsequent ring-closing metathesis with a ruthenium carbene complex affords highly functionalized carbocycles with ring-sizes ranging from five- to eight-membered rings. The application of these methods for the synthesis of carbocyclic natural products from carbohydrates is also demonstrated.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2007
Issue number3
Pages (from-to)399-415
ISSN1434-193X
DOIs
Publication statusPublished - 2007

Keywords

  • Carbocycles
  • Carbohydrates
  • Metathesis
  • Olefination
  • Total synthesis

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