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

被引:169
作者
Rossi, R
Carpita, A
Bellina, F
Stabile, P
Mannina, L
机构
[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
[2] Univ Molise, Fac Sci MFN, I-86170 Isernia, Italy
关键词
isocoumarins; phthalides; iodine; palladium catalysis; cytotoxicity; thunberginols;
D O I
10.1016/S0040-4020(03)00212-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Aryl-4-iodoisocoumarins, which were readily and efficiently prepared by regioselective iodolactonization of methyl 2-ynyl-benzoates 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. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2067 / 2081
页数:15
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