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A Short Synthesis of (+)-Brefeldin C via Enantioselective Radical Hydroalkynylation

preprint
submitted on 01.07.2019 and posted on 02.07.2019 by Lars Gnägi, Severin Vital Martz, Daniel Meyer, Robin Marc Schärer, Philippe Renaud

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows to achieve a high trans diastereoselectivity during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis require six product purifications and it provides (+)-brefeldin C in 18% overall yield.

Funding

The Swiss National Science Foundation (Project 200020_172621)

History

Email Address of Submitting Author

philippe.renaud@dcb.unibe.ch

Institution

University of Bern

Country

Switzerland

ORCID For Submitting Author

0000-0002-9069-7109

Declaration of Conflict of Interest

No conflict of interest

Exports