ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
0/0

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

preprint
submitted on 31.05.2018 and posted on 31.05.2018 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).

History

Email Address of Submitting Author

christopher.dockendorff@mu.edu

Institution

Marquette University

Country

United States

ORCID For Submitting Author

0000-0002-4092-5636

Declaration of Conflict of Interest

A patent application including this work has been submitted.

Exports