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An unprecedented Fe(III)-catalyzed Friedel-Crafts alkylation-hemiketalization-lactonization cascade of electron-rich hydroxy arenes and distinctively functionalized unsaturated 4-keto esters is developed for the construction of polycyclic bridged 2-chromanol lactones. Following this simple and… Click to show full abstract
An unprecedented Fe(III)-catalyzed Friedel-Crafts alkylation-hemiketalization-lactonization cascade of electron-rich hydroxy arenes and distinctively functionalized unsaturated 4-keto esters is developed for the construction of polycyclic bridged 2-chromanol lactones. Following this simple and facile protocol, a broad range of products was prepared in good to excellent yields as a single diastereomer. An unusual conglomerate (enantiomerically pure polymorph) of 3ac is reported along with the absolute stereochemistry, and the remaining products were rigorously confirmed by single-crystal X-ray analysis and analogy.
Journal Title: Organic letters
Year Published: 2019
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