Synthesis of 3-oxosapriparaquinone, a diterpene from Salvia prionitis hance

Article abstract of DOI:10.1246/bcsj.68.2705

12-Acetoxy-5,16-friedo-4,5-seco-abieta-3,5(10),6,8,11,13-hexaene prepared from (+)-dehydroabietic acid, was converted into a natural rearranged abietane-type diterpene, 3-oxosapriparaquinone, via 12-benzoyloxy-3-hydroxy-5,10-friedo-4,5-seco-abieta-5(10),6,8,12-tetra ene-11,14-dione by a series of reactions: hydroboration-oxidation, benzoyl peroxide oxidation, Jones oxidation, and alkaline hydrolysis.