1.1: 100 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 0 °C 2.1: LiN[Si(CH3)3]2 / tetrahydrofuran / -78 °C 2.2: 30 percent / tetrahydrofuran / -78 - 20 °C 3.1: (PhCH2)(Cl)Pd(PPh3)2; LiCl; aq. Na2CO3 / 1,2-dimethoxy-ethane / 86 °C 4.1: 100 percent / H2 / 5 percent Pd/C / ethyl acetate 5.1: aq. LiOH / dioxane / 0 - 20 °C View Scheme

1: triethylamine / dichloromethane / 1.83 h / 0 - 20 °C 2: dimethyl sulfoxide / 72 h / 55 °C / |Inert atmosphere View Scheme

1: diisopropyl azodicarboxylate; PPh3 / tetrahydrofuran / 12 h / 20 °C 2: 4.44 g / aq. NaOH / tetrahydrofuran / 12 h / 20 °C View Scheme

sodium hydroxide; trifluoroacetic acid 1) water, 0 deg C, 14 h, 2) CH2Cl2, 0 deg C, 30 min; Yield given. Multistep reaction;

1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C / |Inert atmosphere 2: lithium hydroxide hydrate / 1,4-dioxane; water / 3 h / 20 °C 3: ammonium hydrogen carbonate; pyridine / 1,4-dioxane / 6 h / 20 °C 4: 2,4,6-trichloro-1,3,5-triazine / N,N-dimethyl-formamide / 1 h / 20 °C View Scheme

1: 93 percent / (COCl)2; Et3N; DMSO / CH2Cl2 / -78 °C 2: 90 percent / DAST / CH2Cl2 / -78 - 20 °C 3: DIBAL-H / tetrahydrofuran / -78 - 20 °C View Scheme

lithium borohydride in tetrahydrofuran T=20°C; 4 h; Inert atmosphere;

1.1: pyridinium chlorochromate / Inert atmosphere 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 1.5 h / -78 - 0 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 3.33 h / 20 °C / Inert atmosphere 4.1: diethyl ether / 0.25 h / 0 °C / Inert atmosphere 5.1: toluene / 6 h / Inert atmosphere; Reflux 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere 7.1: lithium hydroxide hydrate / tetrahydrofuran / 1.5 h / Inert atmosphere 8.1: pyridine / toluene / 2.5 h / Inert atmosphere; Reflux 9.1: diethyl ether / 0.33 h / 0 °C / Inert atmosphere 10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 4 h / 20 °C / Inert atmosphere 11.1: Cu(I)CN / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 11.2: 0.75 h / -78 °C / Inert atmosphere 12.1: dimethylsulfide; oxygen; ozone / methanol; dichloromethane / 2 h / -116 - 20 °C / Inert atmosphere 13.1: diethyl ether / 0 °C / Inert atmosphere 14.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 14.2: 1.5 h / -78 - 0 °C / Inert atmosphere 15.1: triethylsilane; tetrakis(triphenylphosphine) palladium(0); lithium chloride / N,N-dimethyl-formamide / 2 h / 55 °C / Inert atmosphere 16.1: lithium hydroxide hydrate / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere 17.1: trifluoroacetic acid / tetrahydrofuran; dichloromethane / 10 h / Inert atmosphere View Scheme

pyridine in dichloromethane

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / |Inert atmosphere 1.2: 4 h / 0 - 20 °C / |Inert atmosphere 2.1: lithium hydroxide hydrate / tetrahydrofuran / 5 h / 20 °C 2.2: pH 5 View Scheme