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Gold Catalysis for Heterocyclic Chemistry: A Representative Case Study on Pyrone Natural Products
Author(s) -
Fürstner Alois
Publication year - 2018
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.201707260
Subject(s) - chemistry , pyrone , ketone , alkyne , catalysis , ring (chemistry) , ligand (biochemistry) , combinatorial chemistry , organic chemistry , biochemistry , receptor
2‐Pyrones and 4‐pyrones are common structural motifs in bioactive natural products. However, traditional methods for their synthesis, which try to emulate the biosynthetic pathway of cyclization of a 1,3,5‐tricarbonyl precursor, are often harsh and, therefore, not particularly suitable for applications to polyfunctionalized and/or sensitive target compounds. π‐Acid catalysis, in contrast, has proved to be better for a systematic exploration of the pyrone estate. To this end, alkynes are used as stable ketone surrogates, which can be activated under exceedingly mild conditions due to the pronounced carbophilicity of [LAu] + fragments (L=two electron donor ligand); attack of a tethered ester carbonyl group onto the transient alkyne–gold complex then forges the pyrone ring in a fully regiocontrolled manner.