Synthesis of 3-benzoyl-4-benzylfurans structural related to furolignans

Nat Prod Res. 2020 Aug;34(15):2109-2115. doi: 10.1080/14786419.2019.1576040. Epub 2019 Mar 5.

Abstract

Furolignan-type natural products, possessing important biological properties, have been synthesized from a commercially available furan. The elaborated synthetic strategy is based on an innovative Friedel-Crafts reaction starting from an alcohol or a carboxylic acid and triflic anhydride as promoter. Through this synthetic strategy, furolignans having two different aryl groups have been obtained. The products have been evaluated for their antimicrobial properties on Gram positive and Gram negative bacteria, in order to compare their biological activities with those of natural analogues.

Keywords: Friedel-Crafts reaction; anhydride triflic; antimicrobial activity; furan; furolignan; synthesis.

MeSH terms

  • Alcohols / chemistry
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Carboxylic Acids / chemistry
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Lignans / chemistry*
  • Sulfonamides / chemistry

Substances

  • Alcohols
  • Anti-Bacterial Agents
  • Carboxylic Acids
  • Furans
  • Lignans
  • Sulfonamides
  • triflic anhydride
  • furan