Catalytic enantioselective synthesis of functionalized tropanes reveals novel inhibitors of hedgehog signaling

Angew Chem Int Ed Engl. 2013 Dec 2;52(49):12892-6. doi: 10.1002/anie.201307392. Epub 2013 Oct 21.

Abstract

Dipolar cycloaddition: A highly efficient copper(I)-catalyzed enantioselective [3+2] cycloaddition reaction of 1,3-fused cyclic azomethine ylides and nitroalkenes has been developed. This method provides access to functionalized tropane scaffolds with several quaternary and tertiary stereocenters in a single step under mild reaction conditions.

Keywords: asymmetric catalysis; cycloaddition; hedgehog pathway; nitroalkenes; tropanes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cycloaddition Reaction
  • Hedgehog Proteins / antagonists & inhibitors*
  • Hedgehog Proteins / chemistry
  • Hedgehog Proteins / metabolism
  • Molecular Structure
  • Signal Transduction
  • Stereoisomerism
  • Tropanes / chemical synthesis
  • Tropanes / chemistry*
  • Tropanes / pharmacology*

Substances

  • Hedgehog Proteins
  • Tropanes