Synthesis of Functionalized Cannabilactones

Molecules. 2020 Feb 6;25(3):684. doi: 10.3390/molecules25030684.

Abstract

A new approach to synthesize cannabilactones using Suzuki cross-coupling reaction followed by one-step demethylation-cyclization is presented. The two key cannabilactone prototypes AM1710 and AM1714 were obtained selectively in high overall yields and in a lesser number of synthetic steps when compared to our earlier synthesis. The new approach expedited the synthesis of cannabilactone analogs with structural modifications at the four potential pharmacophoric regions.

Keywords: CB2 selective ligands; Suzuki cross-coupling; cannabilactones; cannabinoids.

MeSH terms

  • Cannabinoids / chemical synthesis*
  • Chromones / chemical synthesis

Substances

  • 3-(1,1-dimethyl-heptyl)-1-9-dihydroxy-benzo(c)chromen-6-one
  • 3-(1,1-dimethyl-heptyl)-1-hydroxy-9-methoxy-benzo(c)chromen-6-one
  • Cannabinoids
  • Chromones