3-Aryl-4-iodoisocoumarins, which were readily and efficiently prepd. by regioselective iodolactonization of Me 2-ynylbenzoates or the corresponding carboxylic acids, were used as precursors either to 3-arylisocoumarins, including naturally-occurring thunberginols A and B, or to unsym. 3,4-disubstituted isocoumarins. On the other hand, (Z)- and (E)-3-iodomethylidenephthalides, which were regioselectively prepd. by iodolactonization of Me 2-ethynylbenzoate, were employed as starting materials for the stereospecific synthesis of (Z)- and (E)-3-ylidenephthalides, resp. Some 3-arylisocoumarins and unsym. 3,4-disubstituted isocoumarins showed certain cytotoxic activity against human cancer cell lines in vitro.

Synthesis of 3-arylisocoumarins, including thunberginols A and B, unsummetrical 3,4-disubstituted isocoumarins, and 3-ylidenephthalides via iodolactonization of methyl 2-ynylbenzoates or the corresponding carboxylic acids

ROSSI, RENZO;CARPITA, ADRIANO;BELLINA, FABIO;
2003

Abstract

3-Aryl-4-iodoisocoumarins, which were readily and efficiently prepd. by regioselective iodolactonization of Me 2-ynylbenzoates or the corresponding carboxylic acids, were used as precursors either to 3-arylisocoumarins, including naturally-occurring thunberginols A and B, or to unsym. 3,4-disubstituted isocoumarins. On the other hand, (Z)- and (E)-3-iodomethylidenephthalides, which were regioselectively prepd. by iodolactonization of Me 2-ethynylbenzoate, were employed as starting materials for the stereospecific synthesis of (Z)- and (E)-3-ylidenephthalides, resp. Some 3-arylisocoumarins and unsym. 3,4-disubstituted isocoumarins showed certain cytotoxic activity against human cancer cell lines in vitro.
Rossi, Renzo; Carpita, Adriano; Bellina, Fabio; P., Stabile; L., Mannina
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/204955
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