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