An approach to 3,6-disubstituted 2,5-dioxybenzoquinones via two sequential Suzuki couplings. three-step synthesis of leucomelone

Org Lett. 2009 Feb 5;11(3):589-92. doi: 10.1021/ol802645f.

Abstract

Two sequential Suzuki coupling reactions have been developed for efficient synthesis of synthetically and biologically important 3,6-disubstituted 2,5-dioxybenzoquinone architectures in a highly chemoselective controlled manner. The method serves as a key step in the total synthesis of leucomelone in three steps and in 61% overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoquinones / chemical synthesis*
  • Benzoquinones / chemistry
  • Boronic Acids / chemistry*
  • Catalysis
  • Catechols / chemical synthesis*
  • Catechols / chemistry
  • Combinatorial Chemistry Techniques
  • Molecular Structure

Substances

  • Benzoquinones
  • Boronic Acids
  • Catechols
  • leucomelone