Palladium-Catalyzed Intramolecular Trost-Oppolzer-Type Alder-Ene Reaction of Dienyl Acetates to Cyclopentadienes.
Siddheshwar K BankarBara SinghPinku TungS S V RamasastryPublished in: Angewandte Chemie (International ed. in English) (2018)
A new approach to the synthesis of highly substituted cyclopentadienes, indenes, and cyclopentene-fused heteroarenes by means of the Pd-catalyzed Trost-Oppolzer-type intramolecular Alder-ene reaction of 2,4-pentadienyl acetates is described. This unprecedented transformation combines the electrophilic features of the Tsuji-Trost reaction with the nucleophilic features of the Alder-ene reaction. The overall outcome can be perceived as a hitherto unknown "acid-free" iso-Nazarov-type cyclization. The versatility of this strategy was further demonstrated by the formal synthesis of paucifloral F, a resveratrol-based natural product.