Dearomatizing Conjugate Addition to Quinolinyl Amidines for the Synthesis of Dehaloperophoramidine through Tandem Arylation and Allylation

Dehaloperophoramidine, the dehalogenated analogue of the marine hexacyclic alkaloid perophoramidine was synthesized. The intramolecular nucleophilic dearomatizing arylation of aminoquinoline initiated by a lithium–iodine exchange and the subsequent direct allylation of the resultant azaenolate afforded a pentacyclic bisamidine compound bearing two contiguous all-carbon quaternary centers in good yield with excellent diastereoselectivity.