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.[1]References
- An enantioselective synthesis of tarchonanthuslactone. Garaas, S.D., Hunter, T.J., O'Doherty, G.A. J. Org. Chem. (2002) [Pubmed]
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