Efficient and modular synthesis of new structurally diverse functionalized [n]paracyclophanes by a ring-distortion...

With the goal of synthesizing new [n]paracyclophanes, the expansion of the scope of a strategy originally disclosed by Winterfeldt et al., was investigated. This approach involves sequential Diels-Alder/retro-Diels-Alder reactions, the applications of which have been constrained so far to steroid derivatives. An efficient access to new functionalized [9]-, [10]-, and [16]paracyclophanes, including original cage architectures, was developed from readily available building blocks using thermal electrocyclization and a cycloaddition/cycloreversion sequence as the key steps.