A modified Prins reaction for the facile synthesis of structurally diverse substituted 5-(2-hydroxyethyl)-3,3-dihydrofurane-2(3H)-ones |
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Authors: | Rong Gao |
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Affiliation: | Temple University School of Pharmacy, Department of Pharmaceutical Sciences, 3307 N Broad Street, Philadelphia, PA 19140, USA |
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Abstract: | Furanones are important synthetic intermediates commonly found in natural products, receptor ligands, and drug molecules. Unacceptable yields of substituted furanones obtained using a previously reported Prins reaction led to the development of a modified approach. Readily prepared substituted allylic esters were reacted under Prins reaction conditions catalyzed by a protic acid to provide structurally diverse substituted furanones in modest to good yields. The reaction goes through a protected caprolactone intermediate that was isolated and characterized for selected compounds. The approach supplies an efficient, versatile, and higher yield method for the synthesis of these important heterocyclic intermediates. |
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Keywords: | Modified Prins reaction Substituted furanones Caprolactone intermediates |
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