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Fischer Carbene Catalysis of Alkynol Cycloisomerization:  Application to the Synthesis of the Altromycin B Disaccharide

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journal contribution
posted on 26.04.2007, 00:00 by BonSuk Koo, Frank E. McDonald
The tungsten-catalyzed cycloisomerization of alkynyl alcohols can be conducted without using photochemistry, using a stable tungsten Fischer carbene as the precatalyst for this transformation. A variety of alkynyl alcohols undergo cycloisomerization under these conditions to provide endocyclic enol ethers of five-, six-, and seven-membered ring sizes. The utility of this method is further demonstrated in the stereoselective synthesis of the disaccharide substructure of altromycin B.