Synthesis of natural products containing cyclohexane units utilizing the Ferrier carbocyclization reaction

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Abstract

The Ferrier carbocyclization reaction is one of the most powerful transformations of carbohydrates. This reaction provides enantiomerically pure cyclohexanone derivatives from aldohexoses, and is particularly useful in the chiral pool synthesis of cyclohexane-containing natural products from carbohydrates. We have investigated the synthesis of natural products utilizing the Ferrier carbocyclization reaction. This account provides a brief overview of the Ferrier carbocyclization and its application to natural product synthesis. The utility and versatility of the Ferrier carbocyclization reaction are showcased with the syntheses of hygromycin A, lycoricidine, actinobolin, galanthamine, and morphine starting from carbohydrates.

Original languageEnglish
Pages (from-to)592-605
Number of pages14
JournalChemical record (New York, N.Y.)
Volume14
Issue number4
DOIs
Publication statusPublished - 2014 Aug 1

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Keywords

  • carbohydrates
  • chiral pool
  • Ferrier carbocyclization reaction
  • natural products
  • total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Chemical Engineering(all)
  • Biochemistry, medical
  • Materials Chemistry

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