430425-35-7Relevant academic research and scientific papers
An enantioselective synthesis of tarchonanthuslactone
Garaas, Sarah D.,Hunter, Thomas J.,O'Doherty, George A.
, p. 2682 - 2685 (2002)
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.
