A convenient synthesis of (dl)-3-benzyl-3,4-dihydroisocoumarin as a model of Feralolide

Authors
Rama, NH Iqbal, R Zamani, K Malik, A
Citation
Nh. Rama et al., A convenient synthesis of (dl)-3-benzyl-3,4-dihydroisocoumarin as a model of Feralolide, I J CHEM B, 37(10), 1998, pp. 1021-1023
Citations number
9
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
37
Issue
10
Year of publication
1998
Pages
1021 - 1023
Database
ISI
SICI code
0376-4699(199810)37:10<1021:ACSO(A>2.0.ZU;2-7
Abstract
(dl)-3-Benyl-3,4-dihydroisocoumarin 6, a model of Feralolide, has been synt hesized through 3-benzylisocoumarin 2 which is prepared by the condensation of phenylacetyl chloride with homophthalic acid. Alkaline hydrolysis of 2 yielded the ketoacid 3 which is reduced to racemic hydroxy-acid 5. The latt er is cyclodehydrated to furnish the title compound 6. Isocoumarin 2 and 3, 4-dihydroisocoumarin 6 have been screened in vitro for their antibacterial activity.