2014 · ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

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

Krieger, Jean-Philippe, Ricci, Gino, Lesuisse, Dominique, Meyer, Christophe, Cossy, Janine

Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Année
2014
Volume
53
Numéro
33
Pages
8705-8708
Mois
AUG 11
DOI
10.1002/anie.201401070

Abstract

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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