tetrabutyl ammonium fluoride

1.1: 99 percent / imidazole / dimethylformamide / 20 °C 2.1: 100 percent / quinoline; H2 / 5percent Pd/BaSO4 / methanol / 2 h / 20 °C 3.1: TBAF / tetrahydrofuran / 20 °C 4.1: NaOH / tetrahydrofuran / 3 h / 20 °C 5.1: 62 percent / diethyl ether / 2 h / 0 °C 6.1: 93 percent / imidazole / dimethylformamide / 20 °C 7.1: (+)-(Ipc)2BH / tetrahydrofuran / 2 h / -35 - 0 °C 7.2: MeCHO / tetrahydrofuran / 0 - 40 °C 7.3: 75 percent / tetrahydrofuran / 1 h / 20 °C 8.1: NiCl2(PPh3)2 / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C 9.1: tetrahydrofuran / 20 °C 10.1: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1: tetrahydrofuran / 20 °C 2: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: (+)-(Ipc)2BH / tetrahydrofuran / 2 h / -35 - 0 °C 1.2: MeCHO / tetrahydrofuran / 0 - 40 °C 1.3: 75 percent / tetrahydrofuran / 1 h / 20 °C 2.1: NiCl2(PPh3)2 / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C 3.1: tetrahydrofuran / 20 °C 4.1: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: 95 percent / methanol / 20 °C 2.1: SOCl2 / dimethylformamide; benzene / 2 h / Heating 3.1: PdCl2(PPh3)4 / CHCl3 / Heating 4.1: 81 percent / NaBH4 / methanol / 0.5 h / 0 °C 5.1: t-BuOOH; Ti(OPr)4; D-(-)-DIPT 5.2: Br2 / -78 °C 5.3: TBAF / tetrahydrofuran / -78 °C 6.1: imidazole 7.1: tetrahydrofuran / 20 °C 8.1: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: SOCl2 / dimethylformamide; benzene / 2 h / Heating 2.1: PdCl2(PPh3)4 / CHCl3 / Heating 3.1: 81 percent / NaBH4 / methanol / 0.5 h / 0 °C 4.1: t-BuOOH; Ti(OPr)4; D-(-)-DIPT 4.2: Br2 / -78 °C 4.3: TBAF / tetrahydrofuran / -78 °C 5.1: imidazole 6.1: tetrahydrofuran / 20 °C 7.1: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: PdCl2(PPh3)4 / CHCl3 / Heating 2.1: 81 percent / NaBH4 / methanol / 0.5 h / 0 °C 3.1: t-BuOOH; Ti(OPr)4; D-(-)-DIPT 3.2: Br2 / -78 °C 3.3: TBAF / tetrahydrofuran / -78 °C 4.1: imidazole 5.1: tetrahydrofuran / 20 °C 6.1: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1: imidazole 2: tetrahydrofuran / 20 °C 3: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: t-BuOOH; Ti(OPr)4; D-(-)-DIPT 1.2: Br2 / -78 °C 1.3: TBAF / tetrahydrofuran / -78 °C 2.1: imidazole 3.1: tetrahydrofuran / 20 °C 4.1: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: 81 percent / NaBH4 / methanol / 0.5 h / 0 °C 2.1: t-BuOOH; Ti(OPr)4; D-(-)-DIPT 2.2: Br2 / -78 °C 2.3: TBAF / tetrahydrofuran / -78 °C 3.1: imidazole 4.1: tetrahydrofuran / 20 °C 5.1: 83 percent / TBAF / tetrahydrofuran / 20 °C View Scheme