Efficient synthetic routes to construct multisubstituted benzo[1,2-
b:5,4-
b']difurans and benzo[1,2-
b:4,5-
b']difurans from bis(allyloxy)bis(alkynyl)benzenes or bis(alkynyl)dihydroxybenzenes and allylic halidesutilizing palladium-catalyzed double annulations is reported. By further applying a double ring-closingmetathesis reaction, pentacyclic compounds were also prepared.