Abstract

12-Acetoxy-5,10-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-tetraene-11,14-dione by a series of reactions: hydroboration–oxidation, benzoyl peroxide oxidation, Jones oxidation, and alkaline hydrolysis.

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