The short, efficient total synthesis of (+)‐aquatolide was achieved by a biomimetic transannular 2+2 photocycloaddition, and provides the first example of constructing a 5/5/4/8‐ring system from asteriscunolides. Furthermore, the reaction leading to a 5/4/4/7‐ring system, the originally proposed structure of aquatolide, was also developed. This strategy achieved syntheses of five more humulanolides, (−)‐asteriscunolides A, C, D, and I, and (+)‐tetradehydroasteriscanolide. Short and sweet: The short, efficient total synthesis of (+)‐aquatolide was achieved by a biomimetic transannular 2+2 photocycloaddition, and provides the first example of constructing a 5/5/4/8‐ring system from asteriscunolides. Furthermore, the reaction leading to a 5/4/4/7‐ring system, the originally proposed structure of aquatolide, was also developed. The syntheses of five more humulanolides, (−)‐asteriscunolides A, C, D, and I, and (+)‐tetradehydroasteriscanolide, were also achieved.