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Efficient and Modular Synthesis of New Structurally Diverse Functionalized [n]Paracyclophanes by a Ring-Distortion Strategy


  • J.-P.K. thanks Sanofi for a PhD grant.


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.

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