Formal synthesis of salinosporamide a starting from D-glucose

Takayuki Momose, Yuji Kaiya, Jun Ichi Hasegawa, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

A formal synthesis of salinosporamide A is described. The tertiary alcohol function in salinosporamide A was stereoselectively generated via the substrate control by the reaction of a cyclic ketone derived from D-glucose with Me3Al, and subsequent Overman rearrangement of an allylic trichloroacetimidate effectively constructed the tetrasubstituted carbon with nitrogen. Formation of g-lactam, followed by the introduction of a cyclohexenyl unit furnished the Corey's intermediate of salinosporamide A.

Original languageEnglish
Pages (from-to)2983-2991
Number of pages9
JournalSynthesis
Issue number17
DOIs
Publication statusPublished - 2009 Nov 18

Keywords

  • Carbohydrates
  • Chiral pool
  • Pericyclic reactions
  • Rearrangements
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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