Novel methodology for the synthesis of estrogenic and antiestrogenic isoflav-3-enes

Article abstract of DOI:10.1016/0040-4039(95)01916-6

A novel and selective method for the introduction of substituents at the 2-position of the isoflav-3-ene nucleus, utilizing readily available 3-arylcoumarins as starting materials, is described. Thus, addition of a Grignard reagent to the corresponding phenyl acetal provided the desired 2-alkyl-, alkenyl-, or arylisoflav-3-enes. These compounds interact strongly with the estrogen receptor and show estrogenic or antiestrogenic effects depending upon the nature of the 2-substituent.