Planta Med 2012; 78 - PK2
DOI: 10.1055/s-0032-1321318

Synthesis of γ-benzopyranones using sonogashira coupling and 18-crown-6 ether mediated cyclization

DW Chuang 1, M El-Shazly 1, 2, D Barve Balaji 1, 3, YM Chung 1, FR Chang 1, YC Wu 4
  • 1Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan
  • 2Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, Ain-Shams University, Cairo 11566, Egypt
  • 3Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
  • 4School of Chinese Medicine, College of Chinese Medicine, China Medical University, Taichung 404, Taiwan

An efficient method for the synthesis of γ-benzopyranones and flavones utilizing mild Sonogashira coupling and 18-crown-6 ether mediated 6-endo cyclization of o-alkynoylphenol acetates has been developed. By using this strategy, γ-benzopyranones and flavones bearing electron-donating groups, halogens and simple alkyl substituents were synthesized with satisfactory yields.