Vinyl quinones as Diels-Alder dienes: concise synthesis of (-)-halenaquinone.
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.
Kienzler
Michael A
MA
Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.
Suseno
Sandy
S
Trauner
Dirk
D
D003500:Cyclization; D015394:Molecular Structure; D011809:Quinones / Q000138:chemical synthesis*
D011809:Quinones; C430084:halenaquinone