A d-ribose-derived α-amino nitrile as a versatile intermediate for the collective synthesis of piperidine-type iminosugar C-glycosides

Xiang-Guo Hu, A. Daryl Ariawan, Luke Hunter

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Iminosugar C-glycosides are valuable entities in medicinal chemistry. Herein we disclose a collective synthesis approach to such compounds, in a route that features a remarkably stable, fully characterised, ribose-derived iminium salt as a key intermediate. Addition of organometallic reagents to this key intermediate delivers a variety of iminosugar C-glycoside products in high yields and with excellent stereocontrol.
Original languageEnglish
Pages (from-to)7222-7225
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number52
DOIs
Publication statusPublished - 2014
Externally publishedYes

Keywords

  • Iminosugar
  • Iminocyclitol
  • Polyhydroxylated alkaloid
  • Iminium salt
  • Aminonitrile
  • Ring-closing metathesis

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