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RESEARCH PRODUCT
Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization.
Till OpatzClemes DialerDennis ImbriSteven Peter Hansensubject
chemistry.chemical_classificationAnionsChalconeAlkylationMolecular StructureStereochemistryOrganic ChemistryEtherStereoisomerismStereoisomerismAlkylationRing (chemistry)IsoquinolinesHeterocyclic Compounds 4 or More Ringschemistry.chemical_compoundchemistryCoumarinsCyclizationLamellarin DPyrrolesLactonePyrroleEthersdescription
An electrocyclic ring closure of a 2-azapentadienyl anion generated in situ from a chalcone and glycine ester is the key step of an efficient synthesis of the pyrrole core of the lamellarin alkaloids. A recently developed scalable one-pot procedure provides multigram quantities of a 3,5-diaryl-4-iodopyrrole-2-carboxylate intermediate which is transformed in four further high-yielding operations including a one-pot Pomeranz–Fritsch alkylation/cyclization and an Ullmann-type lactone ring closure into the pentacyclic lamellarin skeleton.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-10-29 | The Journal of organic chemistry |