Synthesis of Multisubstituted Cyclopentadienes from Cyclopentenones Prepared via Catalytic Double Aldol Condensation and Nazarov Reaction Sequence

The rhenium-catalyzed synthesis of cyclopentenone derivatives via double aldol condensation and successive Nazarov reaction is described. The cyclopentenones were converted to the corresponding cyclopentadienes using organolithium reagents. Cyclopentadienes with four different substituents could be synthesized by stepwise double aldol condensation using a ketone and two types of aldehydes, followed by treatment with an organolithium reagent.