1: 98 percent / lithium diisopropylamide / tetrahydrofuran 2: 89 percent / diisobutylaluminium hydride / toluene / 2.5 h / -110 °C 3: 89 percent / tetrahydrofuran / -35 °C 4: 100 percent / acetic acid / H2O / 4 h / Ambient temperature 5: 98 percent / lithium hydroxide monohydrate / H2O; methanol / 24 h / 25 °C 6: triethylamine / CH2Cl2 / 2 h 7: 51 percent / xylene / 11 h / Heating 8: 72 percent / N-chlorosuccinimide, silver nitrate / acetonitrile; H2O / 1.) -5 deg C, 0.5 h, 2.) room temperature, 1 h 9: 95 percent / sodium borohydride / methanol / 0.75 h / -110 °C 10: acetonitrile; pentane / 15 h / Ambient temperature 11: 16.1 mg / anhydrous sodium iodide, chlorotrimethylsilane / acetonitrile / 3.25 h View Scheme

1: 98 percent / lithium hydroxide monohydrate / H2O; methanol / 24 h / 25 °C 2: triethylamine / CH2Cl2 / 2 h 3: 51 percent / xylene / 11 h / Heating 4: 72 percent / N-chlorosuccinimide, silver nitrate / acetonitrile; H2O / 1.) -5 deg C, 0.5 h, 2.) room temperature, 1 h 5: 95 percent / sodium borohydride / methanol / 0.75 h / -110 °C 6: acetonitrile; pentane / 15 h / Ambient temperature 7: 16.1 mg / anhydrous sodium iodide, chlorotrimethylsilane / acetonitrile / 3.25 h View Scheme

1: 89 percent / tetrahydrofuran / -35 °C 2: 100 percent / acetic acid / H2O / 4 h / Ambient temperature 3: 98 percent / lithium hydroxide monohydrate / H2O; methanol / 24 h / 25 °C 4: triethylamine / CH2Cl2 / 2 h 5: 51 percent / xylene / 11 h / Heating 6: 72 percent / N-chlorosuccinimide, silver nitrate / acetonitrile; H2O / 1.) -5 deg C, 0.5 h, 2.) room temperature, 1 h 7: 95 percent / sodium borohydride / methanol / 0.75 h / -110 °C 8: acetonitrile; pentane / 15 h / Ambient temperature 9: 16.1 mg / anhydrous sodium iodide, chlorotrimethylsilane / acetonitrile / 3.25 h View Scheme

1: 89 percent / diisobutylaluminium hydride / toluene / 2.5 h / -110 °C 2: 89 percent / tetrahydrofuran / -35 °C 3: 100 percent / acetic acid / H2O / 4 h / Ambient temperature 4: 98 percent / lithium hydroxide monohydrate / H2O; methanol / 24 h / 25 °C 5: triethylamine / CH2Cl2 / 2 h 6: 51 percent / xylene / 11 h / Heating 7: 72 percent / N-chlorosuccinimide, silver nitrate / acetonitrile; H2O / 1.) -5 deg C, 0.5 h, 2.) room temperature, 1 h 8: 95 percent / sodium borohydride / methanol / 0.75 h / -110 °C 9: acetonitrile; pentane / 15 h / Ambient temperature 10: 16.1 mg / anhydrous sodium iodide, chlorotrimethylsilane / acetonitrile / 3.25 h View Scheme

1: 100 percent / acetic acid / H2O / 4 h / Ambient temperature 2: 98 percent / lithium hydroxide monohydrate / H2O; methanol / 24 h / 25 °C 3: triethylamine / CH2Cl2 / 2 h 4: 51 percent / xylene / 11 h / Heating 5: 72 percent / N-chlorosuccinimide, silver nitrate / acetonitrile; H2O / 1.) -5 deg C, 0.5 h, 2.) room temperature, 1 h 6: 95 percent / sodium borohydride / methanol / 0.75 h / -110 °C 7: acetonitrile; pentane / 15 h / Ambient temperature 8: 16.1 mg / anhydrous sodium iodide, chlorotrimethylsilane / acetonitrile / 3.25 h View Scheme

1: 51 percent / xylene / 11 h / Heating 2: 72 percent / N-chlorosuccinimide, silver nitrate / acetonitrile; H2O / 1.) -5 deg C, 0.5 h, 2.) room temperature, 1 h 3: 95 percent / sodium borohydride / methanol / 0.75 h / -110 °C 4: acetonitrile; pentane / 15 h / Ambient temperature 5: 16.1 mg / anhydrous sodium iodide, chlorotrimethylsilane / acetonitrile / 3.25 h View Scheme

1.1: TMEDA / CH2Cl2 / 2 h / 0 °C 1.2: 78.7 percent / CH2Cl2 / 0 °C 2.1: 96.7 percent / 2,6-lutidine / dimethylformamide / 24 h / 20 °C 3.1: 95.9 percent / LiBH4 / diethyl ether; methanol; tetrahydrofuran / 0 °C 4.1: 95.8 percent / i-Pr2NEt; Py*SO2 / CH2Cl2; dimethylsulfoxide / 0.25 h / 0 °C 5.1: 97.8 percent / TsOH / methanol / 1 h / 20 °C 6.1: 97.1 percent / PPTS / benzene / Heating 7.1: 89.4 percent / NaHCO3; I2 / acetone; H2O / 0.25 h / 0 °C 8.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 8.2: tetrahydrofuran; hexane / -78 - 20 °C 9.1: 2.25 g / TiCl4 / CH2Cl2 / 1 h / -78 °C 10.1: 97 percent / DBU / methanol / 1 h / 0 °C 11.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 11.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 11.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 12.1: 131 mg / (S)-2-methyl-CBS-oxazaborolidine; BH3*Me2S / tetrahydrofuran; toluene / 0.25 h / 0 °C 13.1: 96.4 percent / diethyl ether / 1 h / 0 °C 14.1: 72 percent / Li-naphthalene / tetrahydrofuran / -25 °C 15.1: MnO2 / CH2Cl2 / 3 h / Heating 16.1: 33.6 mg / NaH2PO4; 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O / 20 °C 17.1: NEt3; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 6 h 17.2: 81 percent / DMAP / tetrahydrofuran; toluene / Heating 18.1: 91 percent / aq. HCl / tetrahydrofuran; H2O / 48 h / 20 °C View Scheme

1.1: 96.7 percent / 2,6-lutidine / dimethylformamide / 24 h / 20 °C 2.1: 95.9 percent / LiBH4 / diethyl ether; methanol; tetrahydrofuran / 0 °C 3.1: 95.8 percent / i-Pr2NEt; Py*SO2 / CH2Cl2; dimethylsulfoxide / 0.25 h / 0 °C 4.1: 97.8 percent / TsOH / methanol / 1 h / 20 °C 5.1: 97.1 percent / PPTS / benzene / Heating 6.1: 89.4 percent / NaHCO3; I2 / acetone; H2O / 0.25 h / 0 °C 7.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 7.2: tetrahydrofuran; hexane / -78 - 20 °C 8.1: 2.25 g / TiCl4 / CH2Cl2 / 1 h / -78 °C 9.1: 97 percent / DBU / methanol / 1 h / 0 °C 10.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 10.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 10.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 11.1: 131 mg / (S)-2-methyl-CBS-oxazaborolidine; BH3*Me2S / tetrahydrofuran; toluene / 0.25 h / 0 °C 12.1: 96.4 percent / diethyl ether / 1 h / 0 °C 13.1: 72 percent / Li-naphthalene / tetrahydrofuran / -25 °C 14.1: MnO2 / CH2Cl2 / 3 h / Heating 15.1: 33.6 mg / NaH2PO4; 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O / 20 °C 16.1: NEt3; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 6 h 16.2: 81 percent / DMAP / tetrahydrofuran; toluene / Heating 17.1: 91 percent / aq. HCl / tetrahydrofuran; H2O / 48 h / 20 °C View Scheme

1.1: 46.4 percent / (R,R)-salenCo(III)OAc / H2O / 72 h / 10 - 20 °C 2.1: 99 percent / H2 / Pd/C; Co(OAc)4 / methanol / 20 °C / 760 Torr 3.1: TMSOTf / CH2Cl2; petroleum ether / 2 h 4.1: 2.70 g / NaOMe / methanol / 3 h / 20 °C 5.1: 73.3 percent / DMAP; Et3N / CH2Cl2 / 20 °C 6.1: 86.1 percent / dimethylsulfoxide / 20 °C 7.1: 72.4 percent / cateholborane / 36 h / 20 °C 8.1: 95.4 percent / I2; aq. NaOH / diethyl ether / 0.33 h / 20 °C 9.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 9.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 9.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 10.1: 131 mg / (S)-2-methyl-CBS-oxazaborolidine; BH3*Me2S / tetrahydrofuran; toluene / 0.25 h / 0 °C 11.1: 96.4 percent / diethyl ether / 1 h / 0 °C 12.1: 72 percent / Li-naphthalene / tetrahydrofuran / -25 °C 13.1: MnO2 / CH2Cl2 / 3 h / Heating 14.1: 33.6 mg / NaH2PO4; 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O / 20 °C 15.1: NEt3; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 6 h 15.2: 81 percent / DMAP / tetrahydrofuran; toluene / Heating 16.1: 91 percent / aq. HCl / tetrahydrofuran; H2O / 48 h / 20 °C View Scheme

1.1: 82 percent / H2; n-BuNH2 / Pd/C / ethyl acetate / 3 h / 20 °C / 1551.49 Torr 2.1: DIBALH / diethyl ether / 1 h / -78 °C 2.2: 63 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C 3.1: 93 percent / DMAP; DCC / CH2Cl2 / 3 h / 20 °C 4.1: LHMDS; TMSCl; Et3N / tetrahydrofuran / -78 - 20 °C 4.2: 86 percent / diethyl ether / 0.5 h / 20 °C 5.1: 86 percent / DDQ / CH2Cl2; H2O / 0.33 h / 20 °C 6.1: 84 percent / PhOH / 4.5 h / 125 °C 7.1: 97 percent / NaBH4 / ethanol / 8 h / 20 °C 8.1: 85 percent / I2; Ph3P; imidazole / diethyl ether; acetonitrile / 0.5 h / 20 °C 9.1: 92 percent / LHMDS / tetrahydrofuran / 0.83 h / 0 °C 10.1: 95 percent / Li / tetrahydrofuran; ethanol; liquid ammonia / 0.5 h / -78 °C 11.1: 86 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 12.1: 98 percent / NaI / butan-2-one / 1.5 h / Heating 13.1: 75 percent / urea; NaNO2 / dimethylsulfoxide / 15 h / 20 °C 14.1: 95 percent / imidazole / dimethylformamide / 5 h / 20 °C 15.1: 85 percent / p-chlorophenyl isocyanate; Et3N / benzene / 10 h / Heating 16.1: Mo(CO)6 / H2O; acetonitrile / 1.5 h / Heating 17.1: 35 mg / MsCl; Et3N / CH2Cl2 / 2 h / 20 °C 18.1: 97 percent / PPTS / ethanol / 10 h / 50 °C 19.1: LiOH / H2O; tetrahydrofuran / 0.33 h / 5 °C 20.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C 20.2: 5.5 mg / DMAP / toluene / 14 h / Heating 21.1: 85 percent / NaBH4 / methanol / 0.5 h / -78 °C 22.1: 95 percent / BF3*Et2O; thiophenol / CH2Cl2 / 0.5 h / 20 °C View Scheme