Total synthesis of neurymenolide A based on a gold-catalyzed synthesis of 4-hydroxy-2-pyrones

Angew Chem Int Ed Engl. 2012 Jul 9;51(28):6929-33. doi: 10.1002/anie.201203180. Epub 2012 Jun 4.

Abstract

Treat me gently: for a selective synthesis of the unusually sensitive cyclophanic α-pyrone neurymenolide A, the chosen catalysts must be able to distinguish between six different sites of unsaturation, without scrambling any of the skipped π systems. This challenge was met with a new gold-catalyzed pyrone synthesis in combination with a molybdenum-catalyzed ring-closing alkyne metathesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Catalysis
  • Cyclization
  • Gold / chemistry*
  • Macrolides / metabolism*
  • Molybdenum / chemistry
  • Pyrones / chemical synthesis*
  • Pyrones / metabolism*
  • Stereoisomerism

Substances

  • Alkynes
  • Macrolides
  • Pyrones
  • neurymenolide A
  • Gold
  • Molybdenum