Abstract
A number of 3-homoallyl-2-quinolones have been synthesized from 3-formyl-2-quinolones by reaction with allylindium bromide in aqueous DMF. Intramolecular electrophilic cyclization of these quinolones with iodine afforded either exclusively, or predominantly, racemic cis-diastereoisomers. Nucleophilic substitution reactions at the iodomethyl group afforded a mixture of tetracyclic products and unreacted racemic trans-diastereoisomer.
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