6533b7d7fe1ef96bd1268cc1
RESEARCH PRODUCT
Oxidative Coupling Reactions of 1,3-Diarylpropene Derivatives to Dibenzo[a,c]cycloheptenes by PIFA
Gregor SchnakenburgSiegfried R. WaldvogelSiegfried R. WaldvogelKristina Hackelöersubject
Oxidative cyclizationArylOrganic ChemistryHypervalent moleculefood and beveragesSubstrate (chemistry)chemistry.chemical_elementIodineMedicinal chemistrychemistry.chemical_compoundChemical couplingchemistryYield (chemistry)Organic chemistryheterocyclic compoundsOxidative coupling of methanePhysical and Theoretical Chemistrydescription
The oxidative cyclization reactions of a variety of α-benzyl-cinnamates can be selectively performed with hypervalent iodine as an oxidant. The dibenzo[a,c]cycloheptenes were isolated in up to 55 % yield. When an oxo substrate is applied, the yield was significantly increased. With this synthetic approach, a central intermediate for the synthesis of metasequirin-B was obtained in three steps from very simple starting materials. For this transformation, both aryl moieties have to be activated.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-09-02 | European Journal of Organic Chemistry |