Synthesis of 3-arylisocoumarins, including thunberginols A and B, unsymmetrical 3,4-disubstituted isocoumarins, and 3-ylidenephthalides via iodolactonization of methyl 2-ynylbenzoates or the corresponding carboxylic acids |
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Authors: | Renzo Rossi Adriano CarpitaPaolo Stabile Luisa Mannina |
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Institution: | a Dipartimento di Chimica e Chimica Industriale, University of Pisa, via Risorgimento 35, I-56126 Pisa, Italy b Facoltà di Scienze M.F.N., Università del Molise, via Mazzini 8, 86170 Isernia, Italy |
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Abstract: | 3-Aryl-4-iodoisocoumarins, which were readily and efficiently prepared by regioselective iodolactonization of methyl 2-ynylbenzoates or the corresponding carboxylic acids, were used as precursors either to 3-arylisocoumarins, including naturally-occurring thunberginols A and B, or to unsymmetrical 3,4-disubstituted isocoumarins. On the other hand, (Z)- and (E)-3-iodomethylidenephthalides, which were regioselectively prepared by iodolactonization of methyl 2-ethynylbenzoate, were employed as starting materials for the stereospecific synthesis of (Z)- and (E)-3-ylidenephthalides, respectively. Some 3-arylisocoumarins and unsymmetrical 3,4-disubstituted isocoumarins showed certain cytotoxic activity against human cancer cell lines in vitro. |
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Keywords: | isocoumarins phthalides iodine palladium catalysis cytotoxicity thunberginols |
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