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

Satoshi Imuta, Shinya Ochiai, Miho Kuribayashi, Noritaka Chida

Research output: Contribution to journalArticle

11 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

Fingerprint

Glucose
Enantiomers
Biological Products
Aldehydes
Carbon
actinobolin

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

New synthesis of (-)- and (+)-actinobolin from D-glucose. / Imuta, Satoshi; Ochiai, Shinya; Kuribayashi, Miho; Chida, Noritaka.

In: Tetrahedron Letters, Vol. 44, No. 27, 30.06.2003, p. 5047-5051.

Research output: Contribution to journalArticle

Imuta, Satoshi ; Ochiai, Shinya ; Kuribayashi, Miho ; Chida, Noritaka. / New synthesis of (-)- and (+)-actinobolin from D-glucose. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 27. pp. 5047-5051.
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