A strategy for the synthesis of popolohuanone E:: formal total synthesis of (±)-arenarol

A strategy for the synthesis of popolohuanone E, an oxidatively dimerised arenarol derivative with selective cytotoxic behaviour against non-small cell human lung cancer cells, is described. A known route for the diastereoselective synthesis of the cis-decalin was followed and the subsequent formation of the hindered benzylic bond was illustrated by a formal synthesis of (+/-)-arenarol. Th analogous route directed towards the total synthesis of popolohuanone E is described, along with preliminary model studies concerning the formation of the homo-biaryl nucleus.