1.1: BH3*THF; cyclohexene / tetrahydrofuran / 3 h / 0 - 20 °C 1.2: 90 percent / NaOH; H2O2 / H2O; tetrahydrofuran / 0.75 h / 20 °C 2.1: Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 3.1: tetrahydrofuran / 0.33 h / -78 - 20 °C 4.1: aqueous HF / acetonitrile / 16 h 5.1: 95 percent / DMAP; Et3N / CH2Cl2 / 2 h / 0 °C 6.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 6.2: 60 percent / Cs2CO3; AsPh3 / PdCl2(dppf) / H2O; tetrahydrofuran / 1.5 h 7.1: 93 percent / HF*pyridine / tetrahydrofuran / 36 h / 20 °C 8.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 9.1: 87 percent / TiCl4 / CH2Cl2 / 0.25 h / -78 °C 10.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C 11.1: 91 percent / imidazole / dimethylformamide / 36 h / 20 °C 12.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 13.1: 62 percent / 2 N NaOH / H2O / 1.5 h / Heating 14.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.08 h / 0 °C 14.2: 73 percent / DMAP / toluene; tetrahydrofuran / 0.5 h / 20 °C 15.1: 82 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 2.5 h 16.1: 90 percent / trifluoroacetic acid / CH2Cl2 / 2.5 h / 20 °C 17.1: 30 percent aq. H2O2; KHCO3 / methanol; acetonitrile / 24 h / 20 °C View Scheme

1.1: BH3*THF; cyclohexene / tetrahydrofuran / 3 h / 0 - 20 °C 1.2: 90 percent / NaOH; H2O2 / H2O; tetrahydrofuran / 0.75 h / 20 °C 2.1: Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 3.1: tetrahydrofuran / 0.33 h / -78 - 20 °C 4.1: aqueous HF / acetonitrile / 16 h 5.1: 95 percent / DMAP; Et3N / CH2Cl2 / 2 h / 0 °C 6.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 6.2: 60 percent / Cs2CO3; AsPh3 / PdCl2(dppf) / H2O; tetrahydrofuran / 1.5 h 7.1: 93 percent / HF*pyridine / tetrahydrofuran / 36 h / 20 °C 8.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 9.1: 87 percent / TiCl4 / CH2Cl2 / 0.25 h / -78 °C 10.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C 11.1: 91 percent / imidazole / dimethylformamide / 36 h / 20 °C 12.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 13.1: 62 percent / 2 N NaOH / H2O / 1.5 h / Heating 14.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.08 h / 0 °C 14.2: 73 percent / DMAP / toluene; tetrahydrofuran / 0.5 h / 20 °C 15.1: 82 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 2.5 h 16.1: 90 percent / trifluoroacetic acid / CH2Cl2 / 2.5 h / 20 °C View Scheme