Around and around: A strategy based on sequential Pd‐catalyzed cross‐coupling reactions was applied for the asymmetric synthesis of new macrocyclic meta‐allenophanes composed of 18‐ or 24‐membered rings (see structures). The chiral components, tertiary propargyl alcohols and allene bridges, were assembled by a general enantioselective protocol, which involved a Sharpless epoxidation, an oxidation, and Sonogashira cross‐coupling.