1.1: K2CO3; LiCl / Pd(OAc)2 / dimethylformamide / 100 °C 2.1: 91 percent / aq. HCl / tetrahydrofuran 3.1: NaOH / ethanol 3.2: triphosgene / tetrahydrofuran / 45 °C 3.3: 84 percent / HCl / diethyl ether / 24 h 4.1: 85 percent / Cs2CO3 / dimethylformamide; tetrahydrofuran / 20 °C 5.1: CH3COOH / CH2Cl2 / 24 h 5.2: 90 percent / TFA / CH2Cl2 / 0.5 h 6.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C 6.2: m-CPBA / CH2Cl2 / -78 °C 6.3: 64 percent / Na2CO3 / toluene / Heating 7.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C 8.1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 9.1: DMAP / tetrahydrofuran / 91 h View Scheme

1.1: NaOH / ethanol 1.2: triphosgene / tetrahydrofuran / 45 °C 1.3: 84 percent / HCl / diethyl ether / 24 h 2.1: 85 percent / Cs2CO3 / dimethylformamide; tetrahydrofuran / 20 °C 3.1: CH3COOH / CH2Cl2 / 24 h 3.2: 90 percent / TFA / CH2Cl2 / 0.5 h 4.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C 4.2: m-CPBA / CH2Cl2 / -78 °C 4.3: 64 percent / Na2CO3 / toluene / Heating 5.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C 6.1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 7.1: DMAP / tetrahydrofuran / 91 h View Scheme

palladium 10 on activated carbon; hydrogen in ethyl acetate 18 h;

1: 10 percent 2: 72 percent / H2 / PtO2 / ethanol View Scheme

1: 56 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 2: 10 percent 3: 72 percent / H2 / PtO2 / ethanol View Scheme

1: 1.) t-BuOCl, HCl; 2.) NaBH4 / 1) EtOH 2: 56 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 3: 10 percent 4: 72 percent / H2 / PtO2 / ethanol View Scheme

1: With hydrogenchloride in methanol T=20°C; 17 h; Reflux; 2: With potassium tert-butylate in N,N-dimethyl-formamide T=20°C; 8 h;

1: 71 percent / t-BuOK / dimethylformamide 2: 72 percent / H2 / PtO2 / ethanol View Scheme

1: DMAP / tetrahydrofuran / 91 h View Scheme

1.1: silver trifluoromethanesulfonate / dichloromethane / 20 h / 20 °C / |Inert atmosphere 1.2: 0.75 h / 75 °C / |Inert atmosphere 2.1: 1,2-bis-(diphenylphosphino)ethane; N-ethyl-N,N-diisopropylamine; caesium carbonate; bis(η3-allyl-μ-chloropalladium(II)) / tetrahydrofuran / 20 h / 20 °C / |Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / 20 °C / |Inert atmosphere 3.2: 2 h / -78 - 20 °C / |Inert atmosphere 4.1: trifluoroacetic acid; trifluoroacetic anhydride / dichloromethane / 17 h / 20 °C / |Inert atmosphere 5.1: hydrogen; palladium 10 on activated carbon / ethyl acetate / 18 h View Scheme