Collective enantioselective total synthesis of (+)-sinensilactam A, (+)-lingzhilactone B and (-)-lingzhiol: divergent reactivity of styrene.

The collective total synthesis of (+)-sinensilactam A, (+)-lingzhilactone B, (+)-lingzhilactone C and (-)-lingzhiol has been accomplished from a common epoxide intermediate 9. Chemoselective epoxy opening with either an aryl or alkene moiety of styrene led to different carbon skeletons, which can be advanced to a divergent and concise total synthesis of four meroterpenoids.

Total Synthesis of (±)-Cochlearol A.

Total synthesis of (±)-cochlearol A was accomplished, which features a 6/6 B/D ring synthesis. A TMSOTf-promoted lactonization of -butoxy ketoester produced the desired lactone with quaternary carbon. The configuration of the B/E ring is essential for regioselective B/D ring formation.