Efficient and Modular Synthesis of New Structurally Diverse Functionalized [n]Paracyclophanes by a Ring-Distortion Strategy†
Jean-Philippe Krieger
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)
Search for more papers by this authorDr. Gino Ricci
Sanofi Process Development, 45 Chemin de Mételine BP15, 04210 Sisteron Cedex (France)
Search for more papers by this authorDr. Dominique Lesuisse
R&D Sanofi, 1 Avenue Pierre Brossolette 91385 Chilly-Mazarin Cedex (France)
Search for more papers by this authorCorresponding Author
Dr. Christophe Meyer
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)Search for more papers by this authorCorresponding Author
Prof. Janine Cossy
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)Search for more papers by this authorJean-Philippe Krieger
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)
Search for more papers by this authorDr. Gino Ricci
Sanofi Process Development, 45 Chemin de Mételine BP15, 04210 Sisteron Cedex (France)
Search for more papers by this authorDr. Dominique Lesuisse
R&D Sanofi, 1 Avenue Pierre Brossolette 91385 Chilly-Mazarin Cedex (France)
Search for more papers by this authorCorresponding Author
Dr. Christophe Meyer
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)Search for more papers by this authorCorresponding Author
Prof. Janine Cossy
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)
Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France)Search for more papers by this authorJ.-P.K. thanks Sanofi for a PhD grant.
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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