Multicomponent Double Diels-Alder/Nazarov Tandem Cyclization of Symmetric Cross-Conjugated Diynones to Generate [6-5-6] Tricyclic Products

The construction of complex polycyclic terpenoid products in an efficient and step-economical manner using multicomponent and tandem processes is highly valuable. Herein, we report a tandem cyclization sequence that initiates with a multicomponent double Diels-Alder reaction of cross-conjugated diynones, followed by a Nazarov cyclization to efficiently produce [6-5-6] tricyclic products with excellent regio- and diastereoselectivity. This methodology generates five new carbon-carbon bonds, three rings, quaternary or vicinal quaternary carbons, and stereogenic centers in a one-pot reaction.