Total synthesis of actinobolin from d-glucose by way of the stereoselective three-component coupling reaction

Satoshi Imuta, Hiroki Tanimoto, Miho K. Momose, Noritaka Chida

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The total synthesis of (-)-actinobolin 3, an antipode of the natural product, starting from d-glucose is described. A three-component coupling reaction of functionalized cyclohexenone (+)-6 derived from d-glucose by way of Ferrier's carbocyclization reaction, with vinyl cuprate and 2-alkoxypropanal 7 effectively constructed the carbon framework of 3 in a highly stereoselective manner. In an aldol process of the three-component coupling reaction, stereochemical control (chelation and Felkin-Anh conditions) was achieved by the choice of the protecting groups of a hydroxy function in 2-hydroxypropanal and the reaction solvents. The formal synthesis of the natural enantiomer, (+)-actinobolin 1, starting from d-glucose was also accomplished.

Original languageEnglish
Pages (from-to)6926-6944
Number of pages19
JournalTetrahedron
Volume62
Issue number29
DOIs
Publication statusPublished - 2006 Jul 17

Fingerprint

Glucose
Enantiomers
Chelation
Biological Products
Carbon
actinobolin
3-hydroxybutanal

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Total synthesis of actinobolin from d-glucose by way of the stereoselective three-component coupling reaction. / Imuta, Satoshi; Tanimoto, Hiroki; Momose, Miho K.; Chida, Noritaka.

In: Tetrahedron, Vol. 62, No. 29, 17.07.2006, p. 6926-6944.

Research output: Contribution to journalArticle

Imuta, Satoshi ; Tanimoto, Hiroki ; Momose, Miho K. ; Chida, Noritaka. / Total synthesis of actinobolin from d-glucose by way of the stereoselective three-component coupling reaction. In: Tetrahedron. 2006 ; Vol. 62, No. 29. pp. 6926-6944.
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