Theoretical and experimental determination of the effects governing the transannular Diels-Alder reaction of trans-trans-cis systems with or without activation of the dienophile

A thorough study of the transannular Diels-Alder (TADA) reaction of trans-t rans-cis macrocyclic trienes was carried out. It led to a better understand ing of various parameters that govern the TADA reaction in particular and t he Diels-Alder reaction in general. Thus, carbonyl activation of the dienop hile and substitution of the diene are discussed, as well as the presence o f substituents on the macrocycle and their respective effects at the transi tion-state level.