The total synthesis of asteriscanolide (1) has been achieved by taking advantage on anintermolecular Pauson−Khand cycloaddition and a ring-closing metathesis as key bond-formingtransformations. The approach incorporates the cyclooctane stereogenic center prior to ringformation. Interestingly, the ring-closing metathesis generates a new eight-membered ring withan “in−out” intrabridgehead relationship.