Straightforward synthesis of a double-lasso macrocycle from a nonsymmetrical [c2]daisy chain

Org Lett. 2013 Jan 4;15(1):184-7. doi: 10.1021/ol303186j. Epub 2012 Dec 20.

Abstract

The straightforward synthesis of a double-lasso macrocycle from a nonsymmetrical [c2]daisy chain, using the copper(I)-catalyzed Huisgen alkyne-azide 1,3-dipolar cycloaddition, is described. The preparation of the nonsymmetrical alkyne azide [c2]daisy chain precursor was realized in situ via the exchange of the monomers contained in both symmetrical alkyne and azide [c2]daisy chains and was followed by mass spectrometry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Azides / chemistry*
  • Catalysis
  • Copper / chemistry
  • Cyclization
  • Macrocyclic Compounds / chemical synthesis*
  • Macrocyclic Compounds / chemistry
  • Mass Spectrometry

Substances

  • Alkynes
  • Azides
  • Macrocyclic Compounds
  • Copper