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Efficient and Modular Synthesis of New Structurally Diverse Functionalized [ n ]Paracyclophanes by a Ring‐Distortion Strategy
Author(s) -
Krieger JeanPhilippe,
Ricci Gino,
Lesuisse Dominique,
Meyer Christophe,
Cossy Janine
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201401070
Subject(s) - modular design , cycloaddition , scope (computer science) , ring (chemistry) , combinatorial chemistry , distortion (music) , sequence (biology) , chemistry , computer science , stereochemistry , catalysis , organic chemistry , programming language , amplifier , computer network , biochemistry , bandwidth (computing)
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.