hydrogen; palladium on activated charcoal in ethanol T=70°C;

palladium 10 on activated carbon; hydrogen in ethanol; water T=90°C; P=760.051 Torr; 12 h;

1: With potassium tert-butylate; isopentyl nitrite 2: With acetic acid; zinc in methanol

1.1: pinacolborane; Et3N; 2-(dicyclohexylphosphino)biphenyl / Pd(OAc)2 / dioxane / 80 °C 1.2: 100 percent / aq. Ba(OH)2*8H2O / dioxane / 100 °C 2.1: NaNO2; aq. HCl / tetrahydrofuran / 0 °C 2.2: NaN3 / tetrahydrofuran / 0 - 20 °C 3.1: DIBALH / CH2Cl2 / -78 °C 4.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C 5.1: 100 percent / DCC / CH2Cl2 / 20 °C 6.1: 76 percent / n-Bu3P / toluene / 20 °C 7.1: NaH / dimethylformamide / 0 - 20 °C 8.1: n-BuONO; KHMDS / tetrahydrofuran / 0 °C 9.1: Zn; TFA / CH2Cl2 / 20 °C View Scheme

1.1: pinacolborane; Et3N; 2-(dicyclohexylphosphino)biphenyl / Pd(OAc)2 / dioxane / 80 °C 1.2: 100 percent / aq. Ba(OH)2*8H2O / dioxane / 100 °C 2.1: NaNO2; aq. HCl / tetrahydrofuran / 0 °C 2.2: NaN3 / tetrahydrofuran / 0 - 20 °C 3.1: DIBALH / CH2Cl2 / -78 °C 4.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C 5.1: 100 percent / DCC / CH2Cl2 / 20 °C 6.1: 76 percent / n-Bu3P / toluene / 20 °C 7.1: NaH / dimethylformamide / 0 - 20 °C 8.1: n-BuONO; KHMDS / tetrahydrofuran / 0 °C 9.1: Zn; TFA / CH2Cl2 / 20 °C View Scheme

1: NaH / dimethylformamide / 0 - 20 °C 2: n-BuONO; KHMDS / tetrahydrofuran / 0 °C 3: Zn; TFA / CH2Cl2 / 20 °C View Scheme

1.1: NaNO2; aq. HCl / tetrahydrofuran / 0 °C 1.2: NaN3 / tetrahydrofuran / 0 - 20 °C 2.1: DIBALH / CH2Cl2 / -78 °C 3.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C 4.1: 100 percent / DCC / CH2Cl2 / 20 °C 5.1: 76 percent / n-Bu3P / toluene / 20 °C 6.1: NaH / dimethylformamide / 0 - 20 °C 7.1: n-BuONO; KHMDS / tetrahydrofuran / 0 °C 8.1: Zn; TFA / CH2Cl2 / 20 °C View Scheme

1: DIBALH / CH2Cl2 / -78 °C 2: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C 3: 100 percent / DCC / CH2Cl2 / 20 °C 4: 76 percent / n-Bu3P / toluene / 20 °C 5: NaH / dimethylformamide / 0 - 20 °C 6: n-BuONO; KHMDS / tetrahydrofuran / 0 °C 7: Zn; TFA / CH2Cl2 / 20 °C View Scheme

1: 100 percent / DCC / CH2Cl2 / 20 °C 2: 76 percent / n-Bu3P / toluene / 20 °C 3: NaH / dimethylformamide / 0 - 20 °C 4: n-BuONO; KHMDS / tetrahydrofuran / 0 °C 5: Zn; TFA / CH2Cl2 / 20 °C View Scheme

1.1: ammonium formate; palladium on activated charcoal / water; isopropyl alcohol / 20 °C / |Reflux 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / |Cooling with ice; |Inert atmosphere 3.1: AlCl3, aluminium chloride / 1 h / 100 - 170 °C / |Inert atmosphere 4.1: potassium hexamethylsilazane / toluene / 0.33 h / |Inert atmosphere 4.2: 20 °C / |Inert atmosphere 5.1: palladium on activated charcoal; hydrogenchloride; hydrogen / ethanol / 24 h / 3750.38 Torr / |Autoclave View Scheme