1: 85 percent / HCl / methanol / 15 h / 0 °C 2: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min 3: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C 4: 96 percent / DMAP / pyridine / 3.33 h / 50 °C 5: 96 percent / KOH / methanol / 8.5 h / Ambient temperature 6: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min 7: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature 8: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min 9: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 10: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme

1: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature 2: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min 3: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 4: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme

1: 86 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / 2 °C 2: 99 percent / quinoline, hydrogen / Pd/BaSO4 / 50 h 3: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating 4: 95 percent / m-PCBA / CH2Cl2 / 1 h / 0 °C 5: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature 6: 85 percent / ozone, dimethyl sulfide / CH2Cl2 / 18 h / 40 °C / Heating 7: 91 percent / DBU / CH2Cl2 / 1 h / Ambient temperature 8: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C 9: 85 percent / HCl / methanol / 15 h / 0 °C 10: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min 11: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C 12: 96 percent / DMAP / pyridine / 3.33 h / 50 °C 13: 96 percent / KOH / methanol / 8.5 h / Ambient temperature 14: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min 15: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature 16: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min 17: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 18: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme

1: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min 2: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C 3: 96 percent / DMAP / pyridine / 3.33 h / 50 °C 4: 96 percent / KOH / methanol / 8.5 h / Ambient temperature 5: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min 6: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature 7: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min 8: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 9: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme

1: 96 percent / KOH / methanol / 8.5 h / Ambient temperature 2: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min 3: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature 4: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min 5: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 6: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme

1: 91 percent / DBU / CH2Cl2 / 1 h / Ambient temperature 2: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C 3: 85 percent / HCl / methanol / 15 h / 0 °C 4: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min 5: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C 6: 96 percent / DMAP / pyridine / 3.33 h / 50 °C 7: 96 percent / KOH / methanol / 8.5 h / Ambient temperature 8: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min 9: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature 10: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min 11: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 12: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme

1: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C 2: 85 percent / HCl / methanol / 15 h / 0 °C 3: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min 4: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C 5: 96 percent / DMAP / pyridine / 3.33 h / 50 °C 6: 96 percent / KOH / methanol / 8.5 h / Ambient temperature 7: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min 8: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature 9: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min 10: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 11: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme

1: 96 percent / DMAP / pyridine / 3.33 h / 50 °C 2: 96 percent / KOH / methanol / 8.5 h / Ambient temperature 3: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min 4: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature 5: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min 6: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 7: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme

boron trichloride in hexane; dichloromethane T=-78°C; 4 h;

1: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature 2: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature View Scheme