An enantioselective synthesis of tarchonanthuslactone |
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Authors: | Garaas Sarah D Hunter Thomas J O'Doherty George A |
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Institution: | Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA. |
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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. |
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