1: 70 percent / tetrahydrofuran / Ambient temperature 2: 1) 4N NaOH, 30percent H2O2, 2) Ac2O, pyridine / 1) EtOH, 35 deg C, 4h, 2) RT, overnight 3: 72 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 4: 100 percent / 30percent HClO4 / methanol / 0.17 h / 0 °C 5: 95.5 percent / PDC / CH2Cl2 / 5 h / Ambient temperature 6: 88 percent / H2 / PtO2 / ethyl acetate; ethanol / 3 h / Ambient temperature 7: 96 percent / LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature 8: p-TsOH / 0.33 h / Ambient temperature 9: CrO3, pyridine / 5 h / Ambient temperature 10: 2) 5percent HCl / 2) (PH3P)3RhCl / 1) toluene, 2h, reflux, 2) MeOH, overnight 11: 52 percent / Zn(Hg), TMSCl / tetrahydrofuran / 12 h / Ambient temperature 12: 93 percent / OsO4, NMMNO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 22 h / Ambient temperature View Scheme

1: 1) 4N NaOH, 30percent H2O2, 2) Ac2O, pyridine / 1) EtOH, 35 deg C, 4h, 2) RT, overnight 2: 72 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 3: 100 percent / 30percent HClO4 / methanol / 0.17 h / 0 °C 4: 95.5 percent / PDC / CH2Cl2 / 5 h / Ambient temperature 5: 88 percent / H2 / PtO2 / ethyl acetate; ethanol / 3 h / Ambient temperature 6: 96 percent / LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature 7: p-TsOH / 0.33 h / Ambient temperature 8: CrO3, pyridine / 5 h / Ambient temperature 9: 2) 5percent HCl / 2) (PH3P)3RhCl / 1) toluene, 2h, reflux, 2) MeOH, overnight 10: 52 percent / Zn(Hg), TMSCl / tetrahydrofuran / 12 h / Ambient temperature 11: 93 percent / OsO4, NMMNO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 22 h / Ambient temperature View Scheme

potassium hydroxide 1 h; Heating;

(3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) in water; tert-butyl alcohol 15 h; Ambient temperature;

1: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 2: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 3: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 4: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 5: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 1.36 g / triethylamine / CH2Cl2 / 0.08 h / 0 °C 2: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 3: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 4: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 5: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 6: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 7: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 2: 1.36 g / triethylamine / CH2Cl2 / 0.08 h / 0 °C 3: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 4: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 5: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 6: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 7: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 8: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 2: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 3: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 4: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 80 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 2: 96 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 10 h / Ambient temperature 3: 1.) CH3COOH, H2O, pyridine, 2.) 4-(N,N-dimethylamino)pyridine / 1.) reflux, 4 h, 2.) RT, 10 h 4: 90 percent / SOCl2 / pyridine / 0.5 h / Ambient temperature 5: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 6: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme

1: 45 percent / H2 / 5percent rhodium om alumina / ethyl acetate / 2 h / 2432 Torr 2: 94 percent / 5percent KOH-MeOH / 1 h / Heating View Scheme