Aleurodiscal is one of the representative members of the isopropyl trans-hydrindane sesterterpenoid family. Herein, we describe our efforts towards the synthesis of a complex sesterterpenoid, aleurodiscal. The key precursor of the Cope rearrangement was concisely synthesized from a known bicyclic starting material in 13 linear steps. Our approach highlighted a Van Leusen homologation reaction and an oxidative rearrangement of a tertiary carbinol.