All together: A concise strategy for the first diastereoselective total synthesis of (±)‐schindilactone A is reported. The synthesis features a ring‐closing metathesis, a thiourea/cobalt‐catalyzed Pauson–Khand reaction, and a thiourea/palladium‐catalyzed carbonylative annulation reaction. The chemistry can be applied to the synthesis of structures related to schindilactone A.