Practical and Scalable Total Synthesis of (+)-Dysidavarones A–C

A practical and scalable enantioselective total synthesis of marine anti-cancer sesquiterpene quinone meroterpenoids (+)-dysidavarones A–C was accomplished. The central bridged bicyclo[3.3.1]nonane structure of dysidavarones was efficiently established by a one-pot intermolecular diastereoselective alkylation and intramolecular α-arylation of a Wieland–Miescher ketone derivative without the protection of the C4 carbonyl group with substituted benzyl bromides. (+)-Dysidavarones A and “E” were prepared on a 150-mg scale, which demonstrates the efficiency and reliability of our synthetic route and provides sufficient material of dysidavarones for further bioactivity evaluation.