Title: Regioselective Installation of the Trans-dihydrofuran Architecture for the Synthesis of Resveratrol Oligomers
Description: The family of oligomeric natural products derived from resveratrol possesses broad pharmacological potential, with the larger members of the class often displaying the most impressive bioactivities and the highest potencies. In particular, the trans-dihydrobenzofuran architectural motif, common to the majority of the natural materials, appears to act as a pharmacophore. Our group proposes controlled stepwise synthesis of the resveratrol derivatives to allow access to the higher-order oligomers, bypassing their inefficient isolation from natural sources. Specifically, this work focused on regioselective installation of the trans-dihydrobenzofuran motif on diverse cores. This goal was achieved by employing electrophilic aromatic substitution and directed lithiation as selective functionalization tools. A robust and broadly applicable method has been developed to allow the elaboration of the resulting functional handles into the desired structural motif.