DEGUELIN

• a nicotinamide adenine dinucleotide hydrogen (NADH) dehydrogenase (Complex I) inhibitor to study its effects on mitochondrial respiratory inhibition in human hepatocarcinoma cells (HepG2) and human renal proximal tubule epithelial cells (RPTECs)
• an antiviral compound to study inhibitory effects on human cytomegalovirus (HCMV)-infected human foreskin fibroblast (HFF) cells
• an analytical standard in high-performance liquid chromatography (HPLC)

70191-71-8

522-17-8

Synthesis of (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-9-hydroxy-2,3-dimethoxy-8-(3-methyl-2-buten-1-yl)[1]benzopyrano[3,4-B][1]benzopyridoxol-12(6H)-ones as (6AS,12AS)-6A,12A-dihydropyrano[2,4-B][1]benzopyridoxol-12(6H)-ones 3H-pyrano[2,3-c:6,5-f']dibenzopyran-7(7aH)-one in the following general steps: 1. phenylselenyl chloride (68 mg, 0.35 mmol) was added under argon protection to an anhydrous dichloromethane containing (6AS,12AS)-6A,12A-dihydro-9-hydroxy-2,3-dimethoxy-8-(3-methyl-2-buten-1-yl)[1 ]benzopyrano[3,4-B][1 ]benzopyridoxol-12(6H)-one (128 mg, 0.32 mmol) in an anhydrous dichloromethane solution (4.0 mL) at a reaction temperature of -30 °C with stirring for 10 min. 2. Slowly warm to room temperature and continue stirring for 2 hours followed by 1 hour. 3. remove the solvent under pressure, dissolve the residue in tetrahydrofuran (4.0 mL) and add 30% aqueous hydrogen peroxide solution (0.06 mL) at 0 °C. 4. The reaction mixture was stirred to room temperature, during which the progress of the reaction was monitored by thin layer chromatography (TLC). 5. Upon completion of the reaction, the organic layer was separated by adding ethyl acetate (8.0 mL) and water (4.0 mL). 6. The organic layer was washed sequentially with 5% aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated. 7. The crude product was purified by fast column chromatography (ethyl acetate:hexane=1:2) to afford (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dibenzopyran-7(7aH)-one in the form of a yellowish solid in a yield of 61% (78 mg). Product characterization data: 1H-NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J = 8.7 Hz), 6.77 (s, 1H), 6.62 (d, 1H, J = 10.0 Hz), 6.43 (s, 1H), 6.43 (d, 1H, J = 8.7 Hz), 5.53 (d, 1H, J = 10.0 Hz), 4.89 (m, 1H ), 4.61 (dd, 1H, J = 12.0, 3.1 Hz), 4.17 (d, 1H, J = 12.0 Hz), 3.82 (d, 1H, J = 4.1 Hz), 3.78 (s, 3H), 3.75 (s, 3H), 1.43 (s, 3H), 1.36 (s, 3H). 13C-NMR (CDCl3, 100 MHz) δ 189.2, 160.0, 156.9, 149.4, 147.4, 143.8, 128.6, 128.5, 115.7, 112.7, 111.4, 110.4, 109.1, 104.7, 100.9, 77.6, 72.4, 66.2, 56.3, 55.8, 44.3, 28.4, 28.1. HRMS (FAB) calculated value C23H23O6 (M+H+): 395.1495, measured: 395.1495.