An enantioselective synthesis of tarchonanthuslactone has been achieved in eight steps from ethyl sorbate.The asymmetry of the route was introduced via a Sharplessasymmetric dihydroxylation allowing access to either enantiomer. The synthesis utilizes a palladium-catalyzed reduction and a diastereoselective base-catalyzed acetal formationas the key steps. The pyran ring of tarchonanthuslactonewas established by a Still-olefination/lactonization sequence.DCC-mediated attachment of dihydrocaffeic acid completedthe synthesis of tarchonanthuslactone in a 19% overall yield.