Synthesis of 8β-hydroxy-9(11),13-abietadien-12-one from (+)-dehydroabietylamine and its AhR ligand activity

8β-Hydroxy-9(11),13-abietadien-12-one (1), an abietane diterpenoid and aryl hydrocarbon receptor (AhR) ligand, was synthesized in six steps from commercially available (+)-dehydroabietylamine (2). We used the hypervalent iodine catalyst phenyliodine dicarboxylate, a safer alternative to toxic organoselenide reagents, for oxidative dearomatization of ferruginol (7) compound 1. Compounds 1 2, as well synthetic intermediates (compounds 3–7), were evaluated AhR ligand activity. Only compounds 7 active, which suggests that affinity is influenced by steric environment around C-18 position these compounds.