Xylochemistry-Making Natural Products Entirely from Wood

The first total synthesis of the dimeric berberine alkaloid ilicifoline (ilicifoline B) is reported. Its carbon skeleton is constructed from ferulic acid, veratrole, and methanol. The synthesis reported herein employs starting materials solely derived from wood. The natural product is thus constructed entirely from renewable resources. The same strategy is applied to a formal total synthesis of morphinan alkaloids. The use of wood‐derived building blocks (xylochemicals) instead of the conventional petrochemicals represents a sustainable alternative to classical synthetic approaches. A chip off the old block: A xylochemical approach for the total syntheses of ilicifoline B and morphinans was developed. All of the carbon centers in the final product originate from wood‐based starting materials. These results demonstrate the feasibility and advantages of a xylochemical approach to a sustainable chemical economy and meet the first of four grand challenges in developing a new chemical infrastructure that employs renewable resources.