Ireland-Claisen rearrangement of substrates bearing chiral enol ether units

James P Tellam, David R Carbery

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Abstract

The Ireland-Claisen [3,3]-sigmatropic rearrangement of an allylic glycinate bearing a remote chiral enol ether has been studied. Remote exopericyclic stereocontrol is achievable in this instance. The product from this rearrangement has been progressed through a formal total synthesis of the natural antibiotic, furanomycin.
Original languageEnglish
Pages (from-to)6027-6029
Number of pages3
JournalTetrahedron Letters
Volume52
Issue number45
DOIs
Publication statusPublished - 9 Nov 2011

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Keywords

  • sigmatropic
  • amino acid
  • furanomycin
  • rearrangement
  • Ireland-Claisen

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