A Concise Synthesis of Rhodanthpyrone A and B, Natural 4-(Hydroxyphenyl)-substituted a-Pyrones

Nat Prod Commun. 2017 Jan;12(1):95-98.

Abstract

A concise synthesis of rhodanthpyrone A and B was accomplished via a Suzuki coupling reaction. To find the conditions appropriate to install hydroxyphenyl moieties to the a-pyrone skeleton, a model study was conducted using commercially available boronic acids. It was revealed that the hydroxy moiety of the .pheriylboronic acids should be concealed when reacted with labile 4-tosyl α-pyrone. Consequently, rhodanthpyrone A and B could be synthesized in high. yields by Suzuki reaction using TIPS-protected arylboronic acids. This procedure provided a concise and versatile route for the synthesis of rhodanthpyrones and their 4-aryl substituted a-pyrone analogs.

MeSH terms

  • Boronic Acids / chemistry
  • Catalysis
  • Indicators and Reagents
  • Molecular Structure
  • Palladium / chemistry
  • Pyrones / chemical synthesis*

Substances

  • Boronic Acids
  • Indicators and Reagents
  • Pyrones
  • Palladium