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A concise asymmetric synthesis of (-)-halenaquinone is described. The synthesis features a diastereoselective Heck cyclization to set a quaternary center as well as a novel intramolecular inverse-electron-demand Diels-Alder reaction involving a vinyl quinone. The synthesis is highly convergent and features a minimal amount of protecting group manipulations.


Michael A Kienzler, Sandy Suseno, Dirk Trauner. Vinyl quinones as Diels-Alder dienes: concise synthesis of (-)-halenaquinone. Journal of the American Chemical Society. 2008 Jul 9;130(27):8604-5

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PMID: 18549215

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