Synthesis of 8-desoxythunberginol A and (±)-8-desoxy-3,4- dihydrothunberginol A

Article abstract of DOI:10.1002/jccs.200300046

A two step synthesis of title isocoumarin isolated from Homalium longifolium and its conversion into corresponding 3,4-dihydroisocoumarin has been described. 3,4-Dimethoxybenzoyl chloride on condensation with homophthalic acid afforded 3-(3′,4′-dimethoxyphenyl)isocoumarin which was demethylated to furnish the 8-desoxythunberginol A, whereas its sequential saponification, reduction and demethylation yielded the (±)-8-desoxy-3,4- dihydrothunberginol A. The synthesized compounds were examined in vitro for antibacterial activity.