Versatile and expeditious synthesis of aurones via Au I-catalyzed cyclization

Aurones are conveniently formed in a three-step procedure including a goldI-catalyzed cyclization of 2-(1-hydroxyprop-2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-02, Vol.73 (4), p.1620-1623
Main Authors: Harkat, Hassina, Blanc, Aurélien, Weibel, Jean-Marc, Pale, Patrick
Format: Article
Language:English
Subjects:
Benzofurans - chemical synthesis
Cyclization
Gold - chemistry
Magnetic Resonance Spectroscopy
Spectrometry, Mass, Electrospray Ionization
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Summary:Aurones are conveniently formed in a three-step procedure including a goldI-catalyzed cyclization of 2-(1-hydroxyprop-2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3',4'-tetramethoxyaurone and structure revision of two natural products (dalmaisione D and 4'-chloroaurone) were achieved.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo702197b