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
Тип публикации: Journal Article
Дата публикации: 2003-03-26
scimago Q3
wos Q2
white level БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
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. Graphic
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Rossi R. et al. 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 // Tetrahedron. 2003. Vol. 59. No. 12. pp. 2067-2081.
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Rossi R., Carpita A., Bellina F., Stabile P., Esposito C. 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 // Tetrahedron. 2003. Vol. 59. No. 12. pp. 2067-2081.
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TY - JOUR
DO - 10.1016/S0040-4020(03)00212-6
UR - https://doi.org/10.1016/S0040-4020(03)00212-6
TI - 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
T2 - Tetrahedron
AU - Rossi, Renzo
AU - Carpita, Adriano
AU - Bellina, Fabio
AU - Stabile, Paolo
AU - Esposito, Cristina
PY - 2003
DA - 2003/03/26
PB - Elsevier
SP - 2067-2081
IS - 12
VL - 59
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2003_Rossi,
author = {Renzo Rossi and Adriano Carpita and Fabio Bellina and Paolo Stabile and Cristina Esposito},
title = {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},
journal = {Tetrahedron},
year = {2003},
volume = {59},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/S0040-4020(03)00212-6},
number = {12},
pages = {2067--2081},
doi = {10.1016/S0040-4020(03)00212-6}
}
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MLA
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Rossi, Renzo, et al. “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.” Tetrahedron, vol. 59, no. 12, Mar. 2003, pp. 2067-2081. https://doi.org/10.1016/S0040-4020(03)00212-6.