cis-Dihydrocatechols as precursors to highly oxygenated troponoids: a fully regiocontrolled synthesis of 3,4-dimethoxy-α-tropolone

The highly oxygenated α-tropolone antibiotic 3,4-dimethoxy-α-tropolone 3 has been synthesized in a fully regiocontrolled manner from commercially available cis-1,2-dihydrocatechol 5. Demethylation of 3,4-dimethoxy-α-tropolone 3 produced the potent antitumour agent 3,4-dihydroxy-α-tropolone 4.