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Synthesis of Regioisomeric Functionalized Benzodifurans and Angelicins
Author(s) -
Quezada Elías,
Delogu Giovanna,
Viña Dolores,
Santana Lourdes,
Podda Gianni,
Joao Matos Maria,
Picciau Carmen
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200800421
Subject(s) - chemistry , phloroglucinol , substituent , ring (chemistry) , combinatorial chemistry , stereochemistry , pyrone , organic chemistry
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.