The Reactions of 2-(Trimethylsiloxy)furans with Orthocarboxylic Esters, Acetals, and Acylal in the Presence of Lewis Acids

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Abstract
The reaction of 2-(trimethylsiloxy)furan (1) with orthocarboxylic esters, acetals, and acylal in the presence of Lewis acids afforded the corresponding 4-substituted 2-buten-4-olides. The reaction of 5-methyl-2-(trimethyl-siloxy)furan with orthocarboxylic esters gave unstable 2-substituted 3-penten-4-olides as major products; these gave 2,5-alkanediones upon hydrolysis. The furan (1) also reacted with 1,1-diacetoxy-2-butene to give a mixture of 5-acetoxy-2,6-octadien-4-olide and 7-acetoxy-5-methyl-2,6-heptadien-4-olide. From the former compound, nigrosporalactone was synthesized.

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