Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. 6.6 mL of glacial acetic acid was stirred at 23 C for 18 h. The reaction solution was chilled by the mean of an iceCwater bath and was then treated with saturated aq NaOH until a basic pH was reached. IL20RB antibody The product was extracted with five 20-mL portions of ethyl acetate. The combined organic layer was washed with Pitavastatin calcium kinase activity assay 20 mL of distilled drinking water successively, and 20 mL of brine, and was after that dried out (MgSO4), and focused under reduced pressure to supply 4,5-dimethoxy-2-methyltricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione (10) like a dark yellow essential oil: produce 2.56 g (94%); silica gel TLC 0.20 (3:2 hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) 1.45 (s, 3H), 1.45C1.65 (m, 2H, AB system), 2.80 (d, 1H, = 3.85 Hz),3.06 (br m, 1H), 3.40 (br m, 1H),3.93 (s, 3H), 3.95 (s, 3H), 6.00 (dd, 1H, = 5.5, 3.8 Hz) and 6.14 (dd, 1H, = 5.5, 2.8 Hz); 13C NMR (125 MHz, CDCl3) 26.8,44.5,46.6,49.1, 53.7, 57.3,58.8, 60.9, 134.6, 137.3, 138.27, 138.48, 150.63 and 150.69. 4.1.2. 2-Allyl-4,5-dimethoxy-7-methyltricyclo[6.2.1.02,7]-undeca-4,9-diene-3,6-dione (11) To a stirred option containing 1.00 g (4.04 mmol) of 4,5-dimethoxy-2-methyltricyclo[6.2.1.02,7]-undeca-4,9-diene-3,6-dione (10) in 6 mL of tetrahydrofuran in 0 C, was added portionwise 0.72 g (6.06 mmol) of potassium 0.33 (2:1 hexanes/ethyl acetate); 1H NMR (500 MHz, CDCl3) 1.46 (m, 1H),1.49 (s, 3H), 1.75 (d, 1H, = 9.77 Hz), 2.54 (m, 1H, Abdominal program), 2.66 (m, 1H, AB program),3.01 (s, 1H), 3.10 (s, 1H), 3.88 (s, 3H), 3.89 (s, 3H), 5.04 (m, 2H),5.77 (m, 1H) and 6.04 (s, 2H); 13C NMR (125 MHz, CDCl3) 23.8,41.8,43.4,52.7, 54.4, 56.5, 59.3,60.4, 60.5,95.0, 118.9, 134.2, 137.7, 138.1, 149.5, 150.6 and 177.0; mass range (LCT electrospray), 311.1260 (M+Na)+(C17H20O4Na requires 311.1259). 4.1.3. 2-Allyl-3-methyl-5,6-dimethoxy-1,4-benzoquinone (12) A remedy including 0.91 g (3.17 mmol) of 2-allyl-4,5-dimethoxy-7-methyltricyclo[6.2.1.02,7]-undeca-4,9-diene-3,6-dione (11) in 16 mL of toluene was stirred in reflux for 5 h, where time the response option turned from yellow to dark orange. The solvent was focused under reduced pressure to supply 2-allyl-3-methyl-5,6-dimethoxy-1,4-benzoquinone (12) like a reddish colored essential oil: produce 0.69 g (98%); silica gel TLC 0.38 (2:1 hexanes/ethyl acetate); 1H NMR (500 MHz, CDCl3) 2.02 (s, 3H), 3.23 (d, 2H, = 7.1 Hz), 3.99 (s, 6H),5.04 (m, 2H) and 5.75 (m, 1H); 13C NMR (125 MHz, CDCl3) 12.2, 15.7, 18.2, 30.0, 30.5, 61.4, 116.8, 133.2, 140.0,144.5, 183.7 and 184.6; mass range (LCT electrospray), 223.0962 (M+H)+ (C12H15O4 requires 223.0970). 4.1.4. 1-Allyl-2,3,4,5-tetramethoxy-6-methylbenzene (13) To a vigorously stirred option at 23 C including 0.474 g (2.13 mmol) of 2-allyl-3-methyl-5,6-dimethoxy-1,4-benzoquinone (12) and 0.069 g (0.214 mmol) of 0.63 (2:1 hexane/ethyl acetate); 1H NMR (500 MHz, CDCl3) 2.12 (s, 3H), 3.39 (d, 2H, = 5.9 Hz), 3.76 (s, 3H), 3.78 (s, 3H), 3.88 (s, 3H), 3.89 (s, 3H), 4.92 (d, 1H, = 16.6 Hz), 5.00 (d, 1H, = 9.8 Hz) and 5.92 (m, 1H); 13C NMR (125 MHz, CDCl3) 11.9,31.2, 61.0, 61.3, 61.4, 61.5, 115.0, 125.8, 127.0,136.7, 144.8, 145.4, 148.0 and 148.0; Pitavastatin calcium kinase activity assay mass range (LCT electrospray), 275.1249 (M+Na)+ (C14H20O4Na needs 275.1259). 4.1.5. 1-(3-Hydroxypropyl)-2,3,4,5-tetramethoxy-6-methylbenzene (14)17 To a stirred option including 307 mg (1.22 mmol) of 1-allyl-2,3,4,5-tetramethoxy-6-methylbenzene (13) in 1.8 mL of tetrahydrofuran at 0 C was added dropwise 3.00 mL of the 1.0 M 9-BBN solution in tetrahydrofuran. The response blend was stirred at 23 C for 16 h, at reflux for 2 h then. The reaction solution was treated successively at 0 C with 2 then.0 mL (6.0 mmol) of 3.0 M aq sodium hydroxide and with Pitavastatin calcium kinase activity assay 2 then.0 mL (5.83 mmol) of 30% aq hydrogen peroxide. The response blend was stirred at 0 C 2 C for 0.5 h. The response blend was diluted with 20 mL of distilled drinking water and the merchandise was extracted with four 20-mL servings of ether. The mixed organic layer.