A Scalable Total Synthesis of Deoxyrhapontigenin from Low-Cost a-Resorcylic Acid

A scalable total synthesis for deoxyrhapontigenin (DRG) was successfully accomplished using low-cost a-resorcylic acid as a starting material. Our approach initiates with the protection of phenolic groups using methoxymethyl, resulting in the synthesis of a derivative of the expensive 3,5-hydroxybenzaldehyde, a critical component for Wittig and Perkin approaches in stilbenoid synthesis. Additionally, the corresponding olefin for Heck reaction and formal synthesis of resveratrol were produced in over 85% yield. The synthesis of deoxyrhapontigenin was accomplished in seven steps from the initial carboxylic acid, yielding a product with an average purity higher than 98%, as confirmed by quantitative nuclear magnetic resonance (NMR) analysis.

Keywords:
resveratrol; heck reaction; aerobic oxidation; multigram; Perkins reaction; Wittig reaction