Gold-catalyzed furan/yne cyclizations for the regiodefined assembly of multisubstituted protected 1-naphthols

J Org Chem. 2012 Feb 17;77(4):1915-21. doi: 10.1021/jo202541p. Epub 2012 Feb 6.

Abstract

The gold(I)-catalyzed intramolecular cycloisomerization of furan/ynes bearing a silyloxy or allyloxy group has been developed, which provides a highly efficient access to protected 1-naphthol derivatives with enal or enone moiety. The method offers several advantages such as high stereoselectivities, mild reaction conditions, and easily accessible starting materials. In addition, the naphthyl products could be further transformed into the important benzocoumarins in a one-pot procedure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Catalysis
  • Coumarins / chemical synthesis*
  • Cyclization
  • Furans / chemistry*
  • Gold / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Naphthols / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkynes
  • Coumarins
  • Furans
  • Naphthols
  • Gold