Nine new (±)-8-alkyl-5, 7-dihydroxy-4-(4-hydroxyphenyl)-3, 4-dihydrocoumarins have been synthesized from 2, 4, 6-trimethoxybenzaldehyde via a short, efficient, and regioselective pathway, together with the unsubstituted analogue (±)-5, 7-dihydroxy-4-(4-hydroxyphenyl)-3, 4-dihydrocoumarin. The compounds were tested for estrogenic activity using a yeast-based estrogen screen. Weak estrogenicity was determined for seven members of the series.
