1: 82 percent / TEA, DMAP / CH2Cl2 2: Dess-Martin reagent, t-BuOH / CH2Cl2 3: Zn, TiCl4 / tetrahydrofuran; CH2Cl2 4: 92 percent / aq. HCl / tetrahydrofuran; methanol / 55 °C 5: 89 percent / BCl3 / CH2Cl2 / -78 °C View Scheme

1: tetrahydrofuran / -78 - -65 °C 2: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 3: VO(acac)2, t-BuOOH / CH2Cl2 4: NaH, Bu4NI / dimethylformamide 5: 60 percent / LiH / dimethylformamide / 2 h / 125 °C 6: 82 percent / TEA, DMAP / CH2Cl2 7: Dess-Martin reagent, t-BuOH / CH2Cl2 8: Zn, TiCl4 / tetrahydrofuran; CH2Cl2 9: 92 percent / aq. HCl / tetrahydrofuran; methanol / 55 °C 10: 89 percent / BCl3 / CH2Cl2 / -78 °C View Scheme

1.1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °C / |Inert atmosphere 2.1: potassium carbonate / methanol / 1 h / 20 °C / |Inert atmosphere 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / |Inert atmosphere 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 4.2: 1 h / 0 - 20 °C / |Inert atmosphere 5.1: bis(cyclopentadienyl)titanium dichloride; zinc; 2,4,6-trimethyl-pyridine / tetrahydrofuran / 20 °C / |Inert atmosphere 5.2: 4 h 6.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 6.2: 2 h / 0 - 20 °C / |Inert atmosphere 7.1: (1S)-10-camphorsulfonic acid / methanol / 4 h / 0 - 20 °C / |Inert atmosphere 8.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / |Inert atmosphere 8.2: 0.17 h / -10 °C / |Inert atmosphere 8.3: 4 h / -10 °C / |Inert atmosphere 9.1: formic acid / 9 h / 50 °C / |Inert atmosphere 10.1: sodium methylate / methanol / 0.5 h / 20 °C / |Inert atmosphere View Scheme

1: 92 percent / aq. HCl / tetrahydrofuran; methanol / 55 °C 2: 89 percent / BCl3 / CH2Cl2 / -78 °C View Scheme

1.1: potassium carbonate / methanol / 1 h / 20 °C / |Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / |Inert atmosphere 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 3.2: 1 h / 0 - 20 °C / |Inert atmosphere 4.1: bis(cyclopentadienyl)titanium dichloride; zinc; 2,4,6-trimethyl-pyridine / tetrahydrofuran / 20 °C / |Inert atmosphere 4.2: 4 h 5.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 5.2: 2 h / 0 - 20 °C / |Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / methanol / 4 h / 0 - 20 °C / |Inert atmosphere 7.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / |Inert atmosphere 7.2: 0.17 h / -10 °C / |Inert atmosphere 7.3: 4 h / -10 °C / |Inert atmosphere 8.1: formic acid / 9 h / 50 °C / |Inert atmosphere 9.1: sodium methylate / methanol / 0.5 h / 20 °C / |Inert atmosphere View Scheme

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / |Inert atmosphere 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 2.2: 1 h / 0 - 20 °C / |Inert atmosphere 3.1: bis(cyclopentadienyl)titanium dichloride; zinc; 2,4,6-trimethyl-pyridine / tetrahydrofuran / 20 °C / |Inert atmosphere 3.2: 4 h 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 4.2: 2 h / 0 - 20 °C / |Inert atmosphere 5.1: (1S)-10-camphorsulfonic acid / methanol / 4 h / 0 - 20 °C / |Inert atmosphere 6.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / |Inert atmosphere 6.2: 0.17 h / -10 °C / |Inert atmosphere 6.3: 4 h / -10 °C / |Inert atmosphere 7.1: formic acid / 9 h / 50 °C / |Inert atmosphere 8.1: sodium methylate / methanol / 0.5 h / 20 °C / |Inert atmosphere View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 1.2: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: bis(cyclopentadienyl)titanium dichloride; zinc; 2,4,6-trimethyl-pyridine / tetrahydrofuran / 20 °C / |Inert atmosphere 2.2: 4 h 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 3.2: 2 h / 0 - 20 °C / |Inert atmosphere 4.1: (1S)-10-camphorsulfonic acid / methanol / 4 h / 0 - 20 °C / |Inert atmosphere 5.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / |Inert atmosphere 5.2: 0.17 h / -10 °C / |Inert atmosphere 5.3: 4 h / -10 °C / |Inert atmosphere 6.1: formic acid / 9 h / 50 °C / |Inert atmosphere 7.1: sodium methylate / methanol / 0.5 h / 20 °C / |Inert atmosphere View Scheme

1.1: bis(cyclopentadienyl)titanium dichloride; zinc; 2,4,6-trimethyl-pyridine / tetrahydrofuran / 20 °C / |Inert atmosphere 1.2: 4 h 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 2.2: 2 h / 0 - 20 °C / |Inert atmosphere 3.1: (1S)-10-camphorsulfonic acid / methanol / 4 h / 0 - 20 °C / |Inert atmosphere 4.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / |Inert atmosphere 4.2: 0.17 h / -10 °C / |Inert atmosphere 4.3: 4 h / -10 °C / |Inert atmosphere 5.1: formic acid / 9 h / 50 °C / |Inert atmosphere 6.1: sodium methylate / methanol / 0.5 h / 20 °C / |Inert atmosphere View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 °C / |Inert atmosphere 1.2: 2 h / 0 - 20 °C / |Inert atmosphere 2.1: (1S)-10-camphorsulfonic acid / methanol / 4 h / 0 - 20 °C / |Inert atmosphere 3.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / |Inert atmosphere 3.2: 0.17 h / -10 °C / |Inert atmosphere 3.3: 4 h / -10 °C / |Inert atmosphere 4.1: formic acid / 9 h / 50 °C / |Inert atmosphere 5.1: sodium methylate / methanol / 0.5 h / 20 °C / |Inert atmosphere View Scheme

1.1: (1S)-10-camphorsulfonic acid / methanol / 4 h / 0 - 20 °C / |Inert atmosphere 2.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / |Inert atmosphere 2.2: 0.17 h / -10 °C / |Inert atmosphere 2.3: 4 h / -10 °C / |Inert atmosphere 3.1: formic acid / 9 h / 50 °C / |Inert atmosphere 4.1: sodium methylate / methanol / 0.5 h / 20 °C / |Inert atmosphere View Scheme