Total Synthesis of Sesquilignan threo-(±)-3,4-Divanillyltetrahydrofuran Ferulate

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 (C-6-C-4-C-6), 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-divanillyltetrahydrofuran ferulate. The synthetic method was based on a unified synthetic strategy to obtain target products through 13 steps, in total yield of 8%similar to 9%.