1: Ti(Oi-Pr)4, (-)-diethyl tartrate, t-BuOOH, 4 Angstroem molecular sieves / CH2Cl2 / -20 °C 2: 70 percent / CuCN / diethyl ether; tetrahydrofuran / -12 °C 3: 88 percent / PPTS / Ambient temperature 4: O3 / CH2Cl2 / -78 °C 5: benzene / 65 °C 6: 95 percent / DIBAL-H / toluene / -78 °C 7: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 8: n-BuLi / tetrahydrofuran / -78 - 0 °C 9: TBAF / tetrahydrofuran / Ambient temperature 10: Dess-Martin reagent / CH2Cl2 / 0 °C 11: 93 percent / Ni(acac)2, PPh3, DIBAL-H, 1,3-cyclohexadiene / toluene / 1 h / Ambient temperature 12: imidazole / dimethylformamide 13: O3 / CH2Cl2 / -78 °C 14: t-BuOK / tetrahydrofuran / Ambient temperature 16: TBAF / tetrahydrofuran 17: 95 percent / pyridine; CH2Cl2 / Ambient temperature 18: DOWEX 50WX8 / methanol / 50 °C 19: Et3N / CH2Cl2 20: PPTS / CH2Cl2 / Ambient temperature 21: TBAF / tetrahydrofuran / Ambient temperature 22: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 23: NaH / tetrahydrofuran / Ambient temperature 24: 92 percent / (S)-binaphthol, LiAlH4 / ethanol; tetrahydrofuran / -100 - -78 °C 25: 93 percent / acetic acid / H2O; tetrahydrofuran / 40 °C 26: 95 percent / 1N NaOH / methanol; tetrahydrofuran / Ambient temperature View Scheme

1: Ti(Oi-Pr)4, (-)-diethyl tartrate, t-BuOOH, 4 Angstroem molecular sieves / CH2Cl2 / -20 °C 2: 70 percent / CuCN / diethyl ether; tetrahydrofuran / -12 °C 3: 88 percent / PPTS / Ambient temperature 4: O3 / CH2Cl2 / -78 °C 5: benzene / 65 °C 6: 95 percent / DIBAL-H / toluene / -78 °C 7: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 8: n-BuLi / tetrahydrofuran / -78 - 0 °C 9: TBAF / tetrahydrofuran / Ambient temperature 10: Dess-Martin reagent / CH2Cl2 / 0 °C 11: 93 percent / Ni(acac)2, PPh3, DIBAL-H, 1,3-cyclohexadiene / toluene / 1 h / Ambient temperature 12: imidazole / dimethylformamide 13: O3 / CH2Cl2 / -78 °C 14: t-BuOK / tetrahydrofuran / Ambient temperature 16: TBAF / tetrahydrofuran 17: 95 percent / pyridine; CH2Cl2 / Ambient temperature 18: DOWEX 50WX8 / methanol / 50 °C 19: Et3N / CH2Cl2 20: PPTS / CH2Cl2 / Ambient temperature 21: TBAF / tetrahydrofuran / Ambient temperature 22: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 23: NaH / tetrahydrofuran / Ambient temperature 24: 92 percent / (S)-binaphthol, LiAlH4 / ethanol; tetrahydrofuran / -100 - -78 °C 25: 93 percent / acetic acid / H2O; tetrahydrofuran / 40 °C 26: 95 percent / 1N NaOH / methanol; tetrahydrofuran / Ambient temperature View Scheme

[2,2']bipyridinyl; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; oxygen; copper(I) bromide in acetonitrile T=20°C; 25 h; Schlenk technique;

sodium bis(2-methoxyethoxy)aluminium dihydride in diethyl ether; toluene T=20°C; 16 h;

diisobutylaluminium hydride in dimethyl sulfoxide T=-78°C; 2 h;

diisobutylaluminium hydride in tetrahydrofuran T=0°C; 2 h;

1: pyridinium chlorochromate, sodium acetate / CH2Cl2 / Ambient temperature 2: 1.) sodium hydride / 1.) THF, -78 deg C, 2.) room temperature 3: diisobutylaluminium hydride / toluene / 0 °C View Scheme

1: 1.) sodium hydride / 1.) THF, -78 deg C, 2.) room temperature 2: diisobutylaluminium hydride / toluene / 0 °C View Scheme

1: 83 percent / imidazole / dimethylformamide / 1.) -25 deg C, 1 h, 2.) 0 deg C, 4 h 2: pyridinium chlorochromate, sodium acetate / CH2Cl2 / Ambient temperature 3: 1.) sodium hydride / 1.) THF, -78 deg C, 2.) room temperature 4: diisobutylaluminium hydride / toluene / 0 °C View Scheme

1: Grubb's 2nd generation catalyst / dichloromethane / 3 h / 40 °C / Inert atmosphere 2: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere View Scheme