1.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 1.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 2.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 3.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 4.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 4.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme

1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 2: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 3: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 4: 80 percent / PCC 5: LDA 6: 88 percent / CSA / methanol View Scheme

1.1: tetrahydrofuran / 0.33 h / -78 - 20 °C 2.1: aqueous HF / acetonitrile / 16 h 3.1: 95 percent / DMAP; Et3N / CH2Cl2 / 2 h / 0 °C 4.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 4.2: 60 percent / Cs2CO3; AsPh3 / PdCl2(dppf) / H2O; tetrahydrofuran / 1.5 h 5.1: 93 percent / HF*pyridine / tetrahydrofuran / 36 h / 20 °C 6.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 7.1: 87 percent / TiCl4 / CH2Cl2 / 0.25 h / -78 °C 8.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C 9.1: 91 percent / imidazole / dimethylformamide / 36 h / 20 °C 10.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 11.1: 62 percent / 2 N NaOH / H2O / 1.5 h / Heating 12.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.08 h / 0 °C 12.2: 73 percent / DMAP / toluene; tetrahydrofuran / 0.5 h / 20 °C 13.1: 82 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 2.5 h 14.1: 90 percent / trifluoroacetic acid / CH2Cl2 / 2.5 h / 20 °C 15.1: 30 percent aq. H2O2; KHCO3 / methanol; acetonitrile / 24 h / 20 °C View Scheme

1.1: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C 2.1: 96 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 3.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation 3.2: 37 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C 4.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C 5.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 5.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h 6.1: 92 percent / HF*pyridine / tetrahydrofuran 7.1: 97 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

1.1: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C 2.1: 96 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 3.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation 3.2: 37 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C 4.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C 5.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 5.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h 6.1: 92 percent / HF*pyridine / tetrahydrofuran View Scheme

1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 2: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 3: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 4: 80 percent / PCC 5: LDA View Scheme

1.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 2.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 3.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 4.1: 80 percent / PCC 5.1: LDA 6.1: 88 percent / CSA / methanol 7.1: PCC 7.2: 90 percent / NaClO2 View Scheme

1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 2: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 3: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 4: 80 percent / PCC 5: LDA View Scheme

1.1: 68 percent / PPh3 / CH2Cl2 / 0.25 h / -60 °C 2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 2.2: 65 percent / tetrahydrofuran / 6 h / -78 - 20 °C 3.1: 74 percent / 4 Angstroem molecular sieves; TBAF*3H2O / tetrahydrofuran / 3 h 4.1: 81 percent / DCC; DMAP / CH2Cl2 / 14 h / 20 °C 5.1: 80 percent / CH2Cl2 / [Mo{(t-Bu)(3,5-dimethylphenyl)N}3] / toluene / 8 h / 80 °C 6.1: 99 percent / quinoline; H2 / Lindlar catalyst / hexane; CH2Cl2 / 8 h / 20 °C 7.1: 79 percent / aq. HF / acetonitrile; diethyl ether / 8 h / 20 °C View Scheme

1.1: NaNH2 / tetrahydrofuran / 0.5 h / 20 °C 1.2: 85 percent / tetrahydrofuran / 0.25 h / 20 °C 2.1: 99 percent / TBAF; 4 Angstroem molecular sieves / tetrahydrofuran / 1.33 h / 0 °C View Scheme