Sustainable Production of Bioactive Molecules from C-Lignin-Derived Propenylcatechol

Catechyl lignin (C-lignin) is a naturally occurring linear homogeneous biopolymer composed solely of caffeyl alcohol subunits with cleavable benzodioxane linkages. The inherent structural features of propenylcatechol, a direct depolymerized product of castor seed coats C-lignin, render it a sustainable and promising platform for the synthesis of bioactive molecules. Herein, diversified transformations of propenylcatechol, including C=C bond difunctionalization, beta-modification, beta,gamma-rearrangement, and gamma-methyl derivatization, were reported based on known or developed methods. A series of functional molecular skeletons involved in the current synthetic routes for the preparation of pharmaceuticals and bioactive molecules were obtained. Starting from castor seed coats, annuloline (natural product) and CC-5079 (antitumor) were synthesized using facile and inexpensive reagents in only four- and five-sequence reactions, respectively, thereby demonstrating a superior step-efficiency to that of reported synthetic routes. Almost all atoms in the C-lignin biopolymer were incorporated into the final products owing to the intrinsic structures of naturally occurring C-lignin. Bioactive molecules produced from C-lignin integrate a low-carbon footprint with high-quality and economical manufacture of pharmaceuticals.

Automated summary

Catechyl lignin (C-lignin) is a promising biopolymer for the synthesis of bioactive molecules. Diversified transformations of propenylcatechol, a depolymerized product of C-lignin, were reported, resulting in the preparation of functional molecular skeletons for pharmaceuticals and bioactive molecules. The study demonstrated the low carbon footprint and high-quality production of bioactive molecules from C-lignin.