title: Efficient and modular synthesis of new structurally diverse functionalized [n]paracyclophanes by a ring-distortion strategy.
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.
authors: Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231 Paris Cedex 05 (France).
authors: Jean-Philippe
authors: JP
authors: Krieger
authors: Gino
authors: G
authors: Ricci
authors: Dominique
authors: D
authors: Lesuisse
authors: Christophe
authors: C
authors: Meyer
authors: Janine
authors: J
authors: Cossy
mesh_terms: D003500:Cyclization; D061565:Cycloaddition Reaction; D004988:Ethers, Cyclic / Q000737:chemistry*; D007769:Lactams; D047028:Macrocyclic Compounds / Q000737:chemistry
chemical_list: D004988:Ethers, Cyclic; D007769:Lactams; D047028:Macrocyclic Compounds
keywords: Diels-Alder reaction; electrocyclic reactions; macrocycles; molecular diversity; paracyclophanes