Synthesis of Regioisomeric Functionalized Benzodifurans and Angelicins |
| |
| Authors: | Elías Quezada Giovanna Delogu Dolores Viña Lourdes Santana Gianni Podda Maria Joao Matos Carmen Picciau |
| |
| Affiliation: | 1. Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Cagliari, I‐09124 Cagliari, (phone: +390706758675;2. fax: +390706758553);3. Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, SP‐15782 Santiago de Compostela;4. Departamento de Farmacología, Facultad de Farmacia, Universidad de Santiago de Compostela, SP‐15782 Santiago de Compostela |
| |
| Abstract: | Arenofurans have important biological and pharmacological activities. Compared to benzofurans, the reports on the synthesis of benzodifurans are rather limited. Here, we report the synthesis of a linear and an angular 3,3′‐bis(carboxymethyl)substituted benzodifuran and 4′‐carboxymethyl‐substituted angelicins from phloroglucinol, using 4‐halomethyl‐substituted dipyrones as key intermediates in the synthetic route. This strategy shows that the stability of a pyrone ring depends on the type of substituent at C(4) and the conditions used. |
| |
| Keywords: | Pechmann reaction Benzodifurans Angelicins Ring‐contraction reactions Divergent syntheses |
|
|
