Efficient Stereoselective Synthesis of Brussonol via Cross-Electrophile Regioselective Epoxide Ring-Opening Route

The icetexane diterpenoids include a variety of bioactive and structurally interesting compounds. Its tricyclic skeleton comprises of cyclohexane ring, a central seven-membered ring and an aromatic ring (or a quinone). The significant biological activities possess by these diterpenes are, anti-Chagasic, anticancer, antibacterial, antifungal, and anti-Leishmania activities. Taking into account the biological importance, a number of different approaches to prepare such class of compounds, especially Brussonol and komaroviquinone are described in the literature. Herein, we report a direct and short stereoselective synthesis of brussonol as new anti-Trypanosomal cruzi agent. Our strategy includes regiodivergent epoxide ring-opening with aryl halide via Cross-Electrophile coupling approach, as a key step followed by Marson type cyclization and demethylation reaction.