Enantioselective synthesis of bicyclo[2.2.2]octenones using a copper-mediated oxidative dearomatization/[4 + 2] dimerization cascade.
An enantioselective approach to bicyclo[2.2.2]octenone structures utilizing a copper-mediated asymmetric oxidative dearomatization/[4 + 2] dimerization cascade is described. The total synthesis and absolute stereochemistry reassignment of (+)-aquaticol has been achieved using the methodology.
Dong
Suwei
S
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, USA.
Zhu
Jianglong
J
Porco
John A
JA
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry; D019281:Dimerization; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D034242:Cyclooctanes; D009942:Organometallic Compounds; D003300:Copper