Total Synthesis of the Dilignan threo-(±) -Diferuloysecoisolariciresinol

Threo-(+/-)-diferuloysecoisolariciresinol which belongs to dilignans, has been firstly isolated from the trunk of Machilus thunbergii and exhibits a strong bioactivity. A novel synthetic route to threo-(+/-) -diferuloysecoisolariciresinol using Vanillina as the starting materials was described. The method involved two Stobbe reactions to construct the skeleton of lignan(C-6-C-4-C-6), followed by LiAIH(4) reduction, hydrogenation to form meso- and threo-(+/-)-secoisolanciresinol. threo-(+/-)-Secoisolanciresinol confirmed by NMR, IR and HRMS was the synthetic key intermediate, and then condensated with ferulaic acid to give threo-(+/-) -diferuloysecoisolariciresinol. The synthesis was based on a unified synthetic strategy to obtain target products through 11 steps, with yield of 8%. The synthetic method has the advantages of easy availability of starting materials, simple operation. So it has considerable practical value.