Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 1, Pages 178-198Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02011
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Efficient methods for the synthesis of phenol-derived propiolates and their Au(I)-catalyzed cyclization to give coumarins have been reported. These methods have been successfully applied to the synthesis of natural products such as ayapin and scoparone.
Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.
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