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Stereocontrolled Syntheses of Tetralone‐ and Naphthyl‐Type Lignans by a One‐Pot Oxidative [3,3] Rearrangement/Friedel–Crafts Arylation
Author(s) -
Reddel Jordan C. T.,
Lutz Kelly E.,
Diagne Abdallah B.,
Thomson Regan J.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201307659
Subject(s) - lignan , tetralone , chemistry , friedel–crafts reaction , sigmatropic reaction , oxidative phosphorylation , stereoselectivity , organic chemistry , stereochemistry , catalysis , biochemistry
The development of a stereoselective one‐pot oxidative [3,3] sigmatropic rearrangement/Friedel–Crafts arylation that provides enantioenriched benzhydryl compounds is reported. The utility of this new transformation is demonstrated by the concise synthesis of several tetralone‐ and naphthyl‐type lignan natural products, many of which display anti‐malarial activity.