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Synthesis of substituted 3-furanoates from MBH-acetates of acetylenic aldehydes via tandem isomerization-deacetylation-cycloisomerization: access to Elliott's alcohol


, : Synthesis of substituted 3-furanoates from MBH-acetates of acetylenic aldehydes via tandem isomerization-deacetylation-cycloisomerization: access to Elliott's alcohol. Organic & Biomolecular Chemistry 12(10): 1664-1670

A new method for the synthesis of 5-substituted furan-3-carboxylates from Morita-Baylis-Hillman acetates of acetylenic aldehydes is reported. The process involves palladium-catalyzed isomerization followed by base-promoted deacetylation and cycloisomerization reactions. The utility of this chemistry is further demonstrated by the synthesis of Elliott's alcohol, a key intermediate of the pyrethroid resmethrins.

US$19.90

PMID: 24492976

DOI: 10.1039/c3ob42396d


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