A Short Synthesis of (+)-Brefeldinâ
C through Enantioselective Radical Hydroalkynylation.
Chemistry
; 25(50): 11646-11649, 2019 Sep 06.
Article
em En
| MEDLINE
| ID: mdl-31359455
ABSTRACT
A very concise total synthesis of (+)-brefeldinâ
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 (+)-brefeldinâ
C in 18 % overall yield.
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MEDLINE
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En
Ano de publicação:
2019
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Article