A Short Synthesis of (+)‐Brefeldin C through Enantioselective Radical Hydroalkynylation

Gnägi, Lars; Martz, Severin Vital; Meyer, Daniel; Schärer, Robin Marc; Renaud, Philippe (2019). A Short Synthesis of (+)‐Brefeldin C through Enantioselective Radical Hydroalkynylation. Chemistry - a European journal, 25(50), pp. 11646-11649. Wiley-VCH 10.1002/chem.201903392

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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 a high trans diastereoselectivity to be achieved 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 requires six product purifications and it provides (+)‐brefeldin C in 18 % overall yield.

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