oxygen; sodium hydrogencarbonate; platinum in water; isopropyl alcohol; acetone T=50°C;

1: With lithium hydroxide in tetrahydrofuran; water T=20°C; 8 h; 2: With lithium in ethanol; ammonia T=-78°C; 0.166667 h;

lithium hydroxide in tetrahydrofuran T=20°C; 3.5 h;

ammonia; lithium in ethanol T=-78°C; 0.5 h; Yield given;

1.1: Et3N / diethyl ether / 2 h 2.1: 87 percent / (1R,2S)-ligand-chromium / 40 h / 20 °C 3.1: BH3*THF / tetrahydrofuran / 0 - 20 °C 3.2: 70 percent / aq. HCl / tetrahydrofuran / 3 h / Heating 4.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 4.2: Et3N / CH2Cl2 / -78 - 20 °C 5.1: 71 percent / tetrahydrofuran; hexane / -78 - 20 °C 6.1: Bu3SnCu(Bu)CNLi2 / tetrahydrofuran; hexane / 0.25 h / -78 °C 6.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C 6.3: 80 percent / I2 / diethyl ether / 0 - 20 °C 7.1: 88 percent / Pd(PPh3)4 / benzene; tetrahydrofuran / 0.5 h / 60 - 70 °C 8.1: H2; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr 9.1: 190 mg / CrCl2 / tetrahydrofuran / 20 °C 10.1: 96 percent / Pd(OAc)2; Ag2CO3; Et3N / CH2Cl2 / 24 h / 20 °C 11.1: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C 12.1: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH2Cl2 / 2 h / -10 °C 13.1: PPh3; DEAD / tetrahydrofuran / 3 h / 20 °C 14.1: 93 mg / ammonium molybdate; aq. H2O2 / ethanol; tetrahydrofuran / 20 °C 15.1: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C 16.1: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 17.1: 87 percent / O2; NaHCO3 / Pt / H2O; acetone; propan-2-ol / 50 °C View Scheme

1.1: 71 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: Bu3SnCu(Bu)CNLi2 / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C 2.3: 80 percent / I2 / diethyl ether / 0 - 20 °C 3.1: 88 percent / Pd(PPh3)4 / benzene; tetrahydrofuran / 0.5 h / 60 - 70 °C 4.1: H2; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr 5.1: 190 mg / CrCl2 / tetrahydrofuran / 20 °C 6.1: 96 percent / Pd(OAc)2; Ag2CO3; Et3N / CH2Cl2 / 24 h / 20 °C 7.1: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C 8.1: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH2Cl2 / 2 h / -10 °C 9.1: PPh3; DEAD / tetrahydrofuran / 3 h / 20 °C 10.1: 93 mg / ammonium molybdate; aq. H2O2 / ethanol; tetrahydrofuran / 20 °C 11.1: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C 12.1: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 13.1: 87 percent / O2; NaHCO3 / Pt / H2O; acetone; propan-2-ol / 50 °C View Scheme

1.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 1.2: Et3N / CH2Cl2 / -78 - 20 °C 2.1: 71 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: Bu3SnCu(Bu)CNLi2 / tetrahydrofuran; hexane / 0.25 h / -78 °C 3.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C 3.3: 80 percent / I2 / diethyl ether / 0 - 20 °C 4.1: 88 percent / Pd(PPh3)4 / benzene; tetrahydrofuran / 0.5 h / 60 - 70 °C 5.1: H2; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr 6.1: 190 mg / CrCl2 / tetrahydrofuran / 20 °C 7.1: 96 percent / Pd(OAc)2; Ag2CO3; Et3N / CH2Cl2 / 24 h / 20 °C 8.1: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C 9.1: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH2Cl2 / 2 h / -10 °C 10.1: PPh3; DEAD / tetrahydrofuran / 3 h / 20 °C 11.1: 93 mg / ammonium molybdate; aq. H2O2 / ethanol; tetrahydrofuran / 20 °C 12.1: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C 13.1: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 14.1: 87 percent / O2; NaHCO3 / Pt / H2O; acetone; propan-2-ol / 50 °C View Scheme

1.1: Bu3SnCu(Bu)CNLi2 / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C 1.3: 80 percent / I2 / diethyl ether / 0 - 20 °C 2.1: 88 percent / Pd(PPh3)4 / benzene; tetrahydrofuran / 0.5 h / 60 - 70 °C 3.1: H2; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr 4.1: 190 mg / CrCl2 / tetrahydrofuran / 20 °C 5.1: 96 percent / Pd(OAc)2; Ag2CO3; Et3N / CH2Cl2 / 24 h / 20 °C 6.1: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C 7.1: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH2Cl2 / 2 h / -10 °C 8.1: PPh3; DEAD / tetrahydrofuran / 3 h / 20 °C 9.1: 93 mg / ammonium molybdate; aq. H2O2 / ethanol; tetrahydrofuran / 20 °C 10.1: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C 11.1: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 12.1: 87 percent / O2; NaHCO3 / Pt / H2O; acetone; propan-2-ol / 50 °C View Scheme

1: 88 percent / Pd(PPh3)4 / benzene; tetrahydrofuran / 0.5 h / 60 - 70 °C 2: H2; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr 3: 190 mg / CrCl2 / tetrahydrofuran / 20 °C 4: 96 percent / Pd(OAc)2; Ag2CO3; Et3N / CH2Cl2 / 24 h / 20 °C 5: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C 6: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH2Cl2 / 2 h / -10 °C 7: PPh3; DEAD / tetrahydrofuran / 3 h / 20 °C 8: 93 mg / ammonium molybdate; aq. H2O2 / ethanol; tetrahydrofuran / 20 °C 9: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C 10: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 11: 87 percent / O2; NaHCO3 / Pt / H2O; acetone; propan-2-ol / 50 °C View Scheme

1: H2; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr 2: 190 mg / CrCl2 / tetrahydrofuran / 20 °C 3: 96 percent / Pd(OAc)2; Ag2CO3; Et3N / CH2Cl2 / 24 h / 20 °C 4: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C 5: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH2Cl2 / 2 h / -10 °C 6: PPh3; DEAD / tetrahydrofuran / 3 h / 20 °C 7: 93 mg / ammonium molybdate; aq. H2O2 / ethanol; tetrahydrofuran / 20 °C 8: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C 9: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 10: 87 percent / O2; NaHCO3 / Pt / H2O; acetone; propan-2-ol / 50 °C View Scheme