The use of [XPhosAu(NCMe)]SbF(6) in nitromethane at 100 °C allows the rapid and efficient formation of variously substituted dihydroquinolines, which can be subsequently converted into indoles by a rare photochemical rearrangement.
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Versatile and expeditious synthesis of aurones via Au I-catalyzed cyclization.
J Org Chem
February 2008
Laboratoire de Synthèse et Réactivité Organique, associé au CNRS, Institut de Chimie, Université Louis Pasteur, 4 rue Blaise Pascal, 67000 Strasbourg, France.
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.
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