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

Abstract

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.

isoflavonoids; pterocarpan; DDQ; antitumoral agents; coumestan