Hyperforin is considered the flagship congener among polycyclic polyprenylated acylphloroglucinols due to its compelling and complex molecular architecture, coupled with remarkable biological activity, thus rendering it an appealing synthetic target for chemists over the past two decades. Herein, an innovative linear total synthesis of hyperforin is reported. Our synthesis relies on the formation of the bicyclo[3.3.1]nonane-2,4,9-trione framework via transannular acylation of a decorated eight-membered ring, followed by late stage bridgehead substitution.