An efficient synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol and 1,4-dideoxy-1,4-imino-d- and l-xylitol from chiral aziridines

Hwan Geun Choi, Dong Sik Park, Won Koo Lee, Taebo Sim

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol (d-AB1, 1 and l-AB1, 3) and 1,4-dideoxy-1,4-imino-d- and l-xylitol (d-DIX, 2 and l-DIX, 4) starting from commercially available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered iminosugar ring formation. The facile use of recrystallization to generate pure diastereomers makes the routes more amenable to large-scale synthesis.

Original languageEnglish
Pages (from-to)5775-5777
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number43
DOIs
Publication statusPublished - 2013 Oct 23

Keywords

  • Chiral aziridines
  • Efficient synthesis
  • Natural product
  • d-AB1/l-AB1
  • d-DIX/l-DIX

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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