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Synthesis of a Novel Bicyclic Scaffold Inspired by the Antifungal Natural Product Sordarin

submitted on 31.05.2018, 00:51 and posted on 31.05.2018, 20:58 by Yibiao Wu, Chris Dockendorff
A simplified bicyclic scaffold inspired by the antifungal natural product sordarin was designed and synthesized which maintains the carboxylic acid/aldehyde (or nitrile) pharmacophore. A densely functionalized chiral cyclopentadiene was constructed in 8 steps and utilized in a Diels-Alder reaction with acrylonitrile. The resulting [2.2.1]cycloheptene was transformed into a scaffold possessing vicinal carboxylic acid and nitrile groups, with orientations predicted to provide high affinity for the fungal protein eukaryotic elongation factor 2 (eEF2).


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Marquette University


United States

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Declaration of Conflict of Interest

A patent application including this work has been submitted.