Efficient Method for the Synthesis of Tectorigenin

Abstract

Tectorigenin, isolated from the rhizomes of Belamcanda chinensis, shows a wide variety of biological activities. The interest in its biological activities has been matched by a corresponding interest in its synthesis. We herein reported a convenient synthesis of tectorigenin in good yield. The starting material, 2,4,6‐trihydroxyanisole, gave the intermediate 2,4,4′,6‐tetrahydroxy‐3‐methoxydeoxybenzoin by a Hoesch reaction with 4‐hydroxyphenylacetonitrile. The intermediate was then reacted with methanesulfonyl chloride to produce a mixture of tectorigenin and Ψ‐tectorigenin. Purification of tectorigenin was unnecessary at this stage as Ψ‐tectorigenin in the mixture was isomerized to tectorigenin by refluxing in n‐BuOH in the presence of K₂CO₃.

Keywords:

• isoflavones
• isomerization
• synthesis
• tectorigenin