A New Efficient and Stereoselective Synthesis of Ubiquinone-10

Abstract Coupling reaction of 6-cupro-2,3-dimethoxy-5-methylhydroquinone bis(2-methoxyethoxymethyl) ether with (2E)-1-(phenylsulfonyl)-2-methyl-4-chloro-2-butene afforded the sulfone-functionalized prenylhydro quinone (6) in 82% yield. Stereoselective synthesis of ubiquinone-10 was achieved by the condensation of 6 and solanesyl bromide (yield 92%), reductive elimination of the sulfone group by sodium–ethyl alcohol in THF (yield 80%), and followed by air oxidation of the hydroquinone.