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A Short Synthesis of (+)‐Brefeldin C through Enantioselective Radical Hydroalkynylation
Author(s) -
Gnägi Lars,
Martz Severin Vital,
Meyer Daniel,
Schärer Robin Marc,
Renaud Philippe
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903392
Subject(s) - cyclopentane , enantioselective synthesis , stereocenter , brefeldin a , chemistry , furan , stereochemistry , total synthesis , substituent , yield (engineering) , natural product , organic chemistry , catalysis , materials science , biochemistry , metallurgy , cell , golgi apparatus
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.