Lucía Gurgone, Tonino G Adessi, Josefina Huck, Silvina C Pellegrinet, Agustina La-Venia, Martín J Riveira
Prenylated 2H-pyrans, accessed through a domino Knoevenagel/oxa-6π electrocyclization reaction between 1,3-cyclohexanediones and citral, undergo an electrophilic cascade promoted by N-iodosuccinimide. Iodo-substituted bridged-tricyclic systems are obtained as products of this domino reaction in moderate to good yields and regio- and diastereoselectively, providing a simple synthetic strategy for the construction of heterocyclic frameworks related to biologically active natural products.