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Communication | Special issue | Vol 37, No. 1, 1994, pp.223-226
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S35
Synthesis of Furans from Epoxypropargyl Esters

José M. Aurrecoechea* and Mónica Solay-Ispizua

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad del País Vasco, Apartado 644, 48080 Bilbao, Spain

Abstract

Treatment of 1-(1,2-epoxyalkyl)-2-alkynyl esters with samarium diiodide/Pd° affords E/Z mixtures of 2-alken-4-yn-1-ols where the Z-isomers can be directly transformed into substituted furans. The method is useful for the synthesis of tetrahydroisobenzofurans. A different substitution pattern in the furan nucleus is obtained by application of the same reaction to a regioisomeric 4-(1,2-epoxyalkyl)- 2-alkynyl ester via a cumulene alcohol intermediate.