Acid-catalysed intramolecular addition of β-ketoesters to 1,3-dienes

Org Biomol Chem. 2017 Jan 18;15(3):584-588. doi: 10.1039/c6ob02122k.

Abstract

1,3-Dienyl β-keto esters are cyclised into bicyclolactones using the Bi(OTf)3/TfOH catalytic system. This reaction represents a rare case of simultaneous C-C and C-O bond formation at positions 1 and 3 of a 1,3-diene. Application to the synthesis of ramulosin is presented.

MeSH terms

  • Alkadienes / chemical synthesis*
  • Alkadienes / chemistry
  • Catalysis
  • Cyclization
  • Esters / chemistry*
  • Ketones / chemistry*
  • Mesylates / chemistry*
  • Molecular Structure

Substances

  • Alkadienes
  • Esters
  • Ketones
  • Mesylates
  • Bi(OTf)3
  • trifluoromethanesulfonic acid