6533b821fe1ef96bd127c195
RESEARCH PRODUCT
Protonation and rearrangement of the tricyclo[4.2.2.22,5]dodeca-3,7,9,11-tetraene scaffold
Chunmei GaoHerbert MeierSheyang XuDerong CaoDerong Caosubject
chemistry.chemical_classificationPrimary (chemistry)ChemistryStereochemistryOrganic ChemistryProtonationElectron systemBiochemistryMedicinal chemistryIonHydrolysisDrug DiscoveryEnol etherEther cleavagedescription
The biplanemers 2a,b contain enol ether substructures, which permit facile protonations of the π electron system. The subsequent ether cleavage is characterized by rearrangements of the polycyclic scaffold of the carbenium ions or the electroneutral primary products. Apart from the expected products 3a and 5a, a series of unexpected ketones and diketones (4a′, 9b, 10b, 11b, and 12b) were obtained.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-04-01 | Tetrahedron Letters |