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A divergent approach toward the protecting‐group‐free total synthesis of oxidized benzofulvene sesquiterpenoids is described. Highlight of our synthesis includes regio‐ and stereoselective assembly of the common intermediate 9 by the orchestrated application of a Pd(0)‐catalyzed reductive dehalogenation, a solvent‐free methylenation, and a vinylogous Stork enamine aldol condensation in a substrate‐controlled manner. The advanced intermediate 9 was efficiently transformed to nicotianasesterpenes A, B, and a polygonum sesquiterpenoid, respectively.