Synthesis of Threo-(±)-9,9-Dibenzoylsecoisolariciresinol and its Isomer

Abstract

The total synthesis of threo-(±)-9,9-dibenzoylsecoisolariciresinol and its isomer based on two Stobbe reactions as C–C bond-forming steps used a protected vanillin and diethyl; succinate to give the skeleton of lignan, followed by reduction to afford threo- and meso-(±)-secoisolariciresinol Both were treated with benzoyl chloride to obtain the natural product threo-(±)-9,9-dibenzoylsecoisolariciresinol and Its isomer meso-(±)-9,9-dibenzoylsecoisolariciresinol for the first time.