The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative

we report the first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, a natural isoflavonoid that shows antitumoral activity. the key step involved the heck reaction between the 7,8-dibenzyloxychromen and the organomercurial derived from sesamol, followed by debenzylation. the heck adduct was also employed in the synthesis of the corresponding coumestan derivative, using ddq as oxidant agent.