Enantiospecific Total Synthesis of (-)-Japonicol C.

An efficient and convergent first total syntheses of (±)-japonicol B and (-)-japonicol C have been completed. The notable points of the synthetic route are Lewis-acid-catalyzed Friedel-Crafts reaction for one pot C-C and C-O bond formations resulting in construction of the tricyclic meroterpenoid skeleton, one pot Pd(OH)2/C-catalyzed isomerization/hydrogenation, and site selective sp3 C-H oxidation.