Efficient Synthesis of Cannabigerol, Grifolin, and Piperogalin via Alumina-Promoted Allylation

J Nat Prod. 2020 Sep 25;83(9):2587-2591. doi: 10.1021/acs.jnatprod.0c00131. Epub 2020 Sep 10.

Abstract

The synthesis of three phenolic natural products has been accomplished with unprecedented efficiency using a new alumina-promoted regioselective aromatic allylation reaction. Cannabigerol and grifolin were prepared in one step from the inexpensive 5-alkyl-resorcinols olivetol and orcinol. Piperogalin was synthesized, for the first time, via two sequential allylations of orcinol with geraniol and prenol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aluminum Oxide / chemistry*
  • Cannabinoids / chemical synthesis*
  • Cannabis / chemistry
  • Catalysis
  • Molecular Structure
  • Resorcinols / chemical synthesis*
  • Terpenes / chemical synthesis

Substances

  • Cannabinoids
  • Resorcinols
  • Terpenes
  • piperogalin
  • grifolin
  • cannabigerol
  • Aluminum Oxide