Regioselective synthesis of gentisyl alcohol-type marine natural products

Nat Prod Res. 2019 Jul;33(13):1891-1896. doi: 10.1080/14786419.2018.1478831. Epub 2018 May 25.

Abstract

Gentisyl alcohol-type natural products, possessing various important biological properties, have been synthesized from 4-methoxyphenol by using a selective phenol monohydroxymethylation/monochlorination, a CAN oxidation and a sodium dithionite reduction as the key steps. The natural product synthesis is efficient, atom- and step-economical, and requires no protecting groups.

Keywords: Natural products; chlorination; chlorogentisyl alcohol; gentisyl alcohol; hydroxymethylation; synthesis.

MeSH terms

  • Anisoles / chemistry
  • Benzyl Alcohols / chemical synthesis*
  • Biological Products / chemical synthesis*
  • Halogenation
  • Methylation
  • Oxidation-Reduction

Substances

  • Anisoles
  • Benzyl Alcohols
  • Biological Products
  • mequinol
  • 2,5-dihydroxybenzyl alcohol