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Exploration of synthetic strategies for the stereoselective preparation of novel tetrahydrofuran-containing biaryls: A high-pressure promoted Diels-Alder approach |
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| Authors: | Francesca Piazzolla Carlo Siciliano Lucio Minuti Andrea Temperini |
| Institution: | 1. Dipartimento di Scienze Farmaceutiche, Università di Perugia, via del Liceo 1, 06123 Perugia, Italy;2. Dipartimento di Farmacia e Scienze della Salute e della Nutrizione, Università della Calabria, Edificio Polifunzionale, 87030 Arcavacata di Rende, Cosenza, Italy;3. Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, via Elce di Sotto 8, 06123 Perugia, Italy |
| Abstract: | Three stereoselective synthetic approaches to tetrahydrofuran-containing biaryl scaffolds are described. All approaches involve a high-pressure promoted Diels-Alder reaction of substituted diene with methyl propiolate to give, after aromatization, the corresponding biaryl. The tetrahydrofuran moiety can be created starting from aryl-Br or aryl-CO2Me functional groups through a γ-phenylseleno ketone intermediate. |
| Keywords: | Biaryls Tetrahydrofuran High-pressure Diels-Alder Selenones |
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