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Divergent and stereoselective synthesis of dafachronic acids
Authors:Antimo GioielloPaola Sabbatini  Emiliano RosatelliAntonio Macchiarulo  Roberto Pellicciari
Institution:Dipartimento di Chimica e Tecnologia del Farmaco, Università di Perugia, Via del Liceo 1, 06123 Perugia, Italy
Abstract:A new divergent synthesis of DAF-12 ligands, namely Δ4- and Δ7-dafachronic acid, is described starting from the natural bile acid hyodeoxycholic acid. Homologation of the side chain followed by stereoselective reduction of the Δ24 olefinic linkage, 6α-dehydroxylation and C3-oxidation affords dafachronic acids in good yields and high diastereoselectivity making this approach easily accessible and scalable.
Keywords:Δ4-Dafachronic acid  Δ7-Dafachronic acid  DAF-12  Stereoselective hydrogenation
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