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
| Autor: | Luisa Mannina, Paolo Stabile, Adriano Carpita, Renzo Rossi, Fabio Bellina |
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| Rok vydání: | 2003 |
| Předmět: |
iodine
Stereochemistry Organic Chemistry Isocoumarins Iodolactonization Halogenation thunberginols chemistry.chemical_element Regioselectivity General Medicine phthalides isocoumarins palladium catalysis cytotoxicity Iodine Biochemistry 3-Aryl-4-iodoisocoumarins Stereospecificity chemistry Drug Discovery Organic chemistry Cytotoxicity Human cancer |
| Zdroj: | Tetrahedron. 59:2067-2081 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/s0040-4020(03)00212-6 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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