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Synfacts 2008(10): 1084-1084  
DOI: 10.1055/s-2008-1078229
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Zn-Catalyzed Cycloisomerizations in the Synthesis of Substituted Furans

Contributor(s): Paul Knochel, Andreas J. Wagner
A. Sniady, A. Durham, M. S. Morreale, A. Marcinek, S. Szafert, T. Lis, K. R. Brzezinska, T. Iwasaki, T. Ohshima, K. Mashima, R. Dembinski*
Oakland University, Rochester and University of California, Berkeley, USA; Technical University of Lodz and University of Wroclaw, Poland; Osaka University, Japan
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Publikationsdatum:
22. September 2008 (online)

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Significance

The 5-endo-dig cycloisomerization of 1,4- and 1,2,4- mostly aryl-substituted but-3-yn-1-ones in the presence of catalytic amounts of zinc chloride etherate in CH2Cl2 at room temperature gives 2,5-di- and 2,3,5-trisubstituted furans in high yields (85-97%). The reaction is also applicable to the synthesis of bicyclic furopyrimidine nucleosides starting from 5-alkynyl-2′-deoxy­uridines.