Synthesis of Regioisomeric Functionalized Benzodifurans and Angelicins

✍ Scribed by Elías Quezada; Giovanna Delogu; Dolores Viña; Lourdes Santana; Gianni Podda; Maria Joao Matos; Carmen Picciau

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: German
• Weight: 146 KB
• Volume: 92
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200800421

✦ Synopsis

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.