title: An enantioselective synthesis of tarchonanthuslactone.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
authors.forename: Sarah D
authors.initials: SD
authors.lastname: Garaas
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Hunter
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty