New synthesis of (-)- and (+)-actinobolin from D-glucose

Satoshi Imuta, Shinya Ochiai, Miho Kuribayashi, Noritaka Chida

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The total synthesis of (-)-actinobolin 2, an antipode of the natural product starting from D-glucose is described. A three-component coupling reaction of a functionalized cyclohexenone (+)-6, derived from D-glucose by way of Ferrier's carbocyclization, with vinyl cuprate and an aldehyde (R)-5 effectively constructed the carbon framework of 2 in a highly stereoselective manner. The formal synthesis of the natural enantiomer 1 from D-glucose was also achieved.

Original languageEnglish
Pages (from-to)5047-5051
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number27
DOIs
Publication statusPublished - 2003 Jun 30

Keywords

  • Actinobolin
  • Carbohydrate
  • Ferrier's carbocyclization
  • Three-component coupling reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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