Vinyl quinones as Diels-Alder dienes: concise synthesis of (-)-halenaquinone.

Abstract

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. 
DOI: 10.1021/ja8035042

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