Synthesis of Natural Products Containing Cyclohexane Units Starting from Aldohexoses

Noritaka Chida, Seiichiro Ogawa

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Preparation of optically active, highly functionalized carbocycles is an important issue in recent synthetic organic chemistry. Ferrier's carbocyclization reaction, which provides optically pure cyclohexanones from aldohexoses, is one of the most efficient procedures for this purpose. Chiral and highly oxygenated cyclohexanes obtained by this reaction are potentially versatile chiral building blocks in natural product synthesis. In this article, the development of catalytic Ferrier's carbocyclization reaction with mercury (II) trifluoroacetate, and total syntheses of natural products containing cyclohexane units (hygromycin A, lycoricidine, and mesembranol) starting from aldohexoses using this reaction as the key steps are described The methodology described in this article extends the usefulness of carbohydrates as chiral building blocks to the synthesis of natural products possessing cyclohexane rings in optically active forms.

Original languageEnglish
Pages (from-to)858-868
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume53
Issue number10
DOIs
Publication statusPublished - 1995 Jan 1

Keywords

  • Aldohexoses
  • Carbohydrates
  • Chiral building block
  • Ferrier's carbocyclization reaction
  • Functionalized carbocycles
  • Hygromycin A
  • Lycoricidine
  • Mesembranol
  • Natural product synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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