An Enantioselective Synthesis of Tarchonanthuslactone

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