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Highly Enantioselective Catalytic Vinylogous Propargylation of Coumarins Yields a Class of Autophagy Inhibitors
Author(s) -
Xu Hao,
Laraia Luca,
Schneider Laura,
Louven Kathrin,
Strohmann Carsten,
Antonchick Andrey P.,
Waldmann Herbert
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706005
Subject(s) - enantioselective synthesis , catalysis , combinatorial chemistry , natural product , chemistry , autophagy , organic chemistry , stereochemistry , biochemistry , apoptosis
A highly enantioselective copper‐catalyzed vinylogous propargylic substitution has been developed. Aromatic and aliphatic propargylic esters react smoothly with substituted coumarins under mild reaction conditions to give the desired products with excellent yields and enantioselectivities. Subsequent single‐step transformations enable the synthesis of a wide range of multifunctional and diverse compounds, and allow the efficient combination of different natural product fragments. Investigation of the obtained compound collection in cell‐based assays monitoring changes in phenotype led to the discovery of a novel class of autophagy inhibitors.