aluminium trichloride in dichloromethane 2 h; Ambient temperature;

1: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 2: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 3: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 4: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 5: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 6: 3 N HCl / ethyl acetate / 1 h / 25 °C 7: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C 8: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C View Scheme

1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 6 h / Heating 2: m-chloroperbenzoic acid (mCPBA) / CH2Cl2 / 24 h / 40 °C 3: HCl / methanol / 3 h / 25 °C 4: H2 / 10percent Pd/C / methanol / 6 h / 25 °C 5: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 6: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 7: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 8: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 9: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 10: 3 N HCl / ethyl acetate / 1 h / 25 °C 11: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C 12: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C View Scheme

1: H2 / 10percent Pd/C / methanol / 6 h / 25 °C 2: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 3: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 4: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 5: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 6: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 7: 3 N HCl / ethyl acetate / 1 h / 25 °C 8: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C 9: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C View Scheme

1: m-chloroperbenzoic acid (mCPBA) / CH2Cl2 / 24 h / 40 °C 2: HCl / methanol / 3 h / 25 °C 3: H2 / 10percent Pd/C / methanol / 6 h / 25 °C 4: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 5: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 6: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 7: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 8: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 9: 3 N HCl / ethyl acetate / 1 h / 25 °C 10: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C 11: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C View Scheme

1: HCl / methanol / 3 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 6 h / 25 °C 3: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 4: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 5: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 6: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 7: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 8: 3 N HCl / ethyl acetate / 1 h / 25 °C 9: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C 10: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C View Scheme

1: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 2: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 3: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 4: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 5: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 6: 3 N HCl / ethyl acetate / 1 h / 25 °C 7: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C 8: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C View Scheme

1: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 2: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 3: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 4: 3 N HCl / ethyl acetate / 1 h / 25 °C 5: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C 6: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C View Scheme

1: 63 percent / N,N-dicyclohexylcarbodimide / dioxane / 4 h / Ambient temperature 2: 24 percent / 1N aq. NaOH / methanol; acetonitrile / 0.5 h / Ambient temperature 3: 6.1 mg / H2 / 5percent Pd/C / methanol / 3 h / Ambient temperature 4: 39 percent / N,N-dicyclohexylcarbodimide / dioxane / 15 h 5: 60 percent / AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: NaH, CuBr-SMe2, collidine / 8 h / 130 °C 2: 98 percent / H2 / 10percent Pd/C / methanol / 6 h / 25 °C / 760 Torr 3: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 4: LiOH*H2O / tetrahydrofuran; methanol; H2O / 2 h / 25 °C 5: HCl / ethyl acetate / 1 h / 25 °C 6: 58 percent / DPPA, NaHCO3 / dimethylformamide / 72 h / 0 °C 7: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 0 °C View Scheme