A method for the synthesis of natural product 3,4-divanillyltetrahydrofuran ferulate was presented. Using vanillina as the material and through two Stobbe reactions to construct the skeleton of lignan (C₆-C₄-C₆), followed by hydrogenation, LiAlH₄ reduction and separation via flash column chromatography, meso- and threo-(±)-secoisolarciresinols were obtained. Meso- or threo-(±)-secoisolarciresinol was reacted with TsCl, respectively, to give the key intermediate meso- or threo-(±)-shonanin, which was then condensed with ferulaic acid to obtain sesquilignan threo- or its analogue erythro-(±)-3,4-divanillyltetrahy- drofuran ferulate. The synthetic method was based on a unified synthetic strategy to obtain target products through 13 steps, in total yield of 8%～9%.

Key words: total synthesis, 3,4-divanillyltetrahydrofuran ferulate, Stobbe reaction, sesquilignan