sodium hydride in N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h;

1: 3,4-(methylenedioxy)phenol With sodium hydride in tetrahydrofuran; DMF (N,N-dimethyl-formamide) T=0 - 20°C; 0.5 h; 2: chloromethyl methyl ether in tetrahydrofuran; DMF (N,N-dimethyl-formamide) T=20°C; 1 h;

1: potassium hydroxide / methanol; H2O 2: 4.7 g / ethyldiisopropylamine / CH2Cl2 / 0 - 20 °C View Scheme

1: m-chloroperoxybenzoic acid / CH2Cl2 / 18 h / Heating 2: potassium hydroxide / methanol; H2O 3: 4.7 g / ethyldiisopropylamine / CH2Cl2 / 0 - 20 °C View Scheme

n-butyllithium in tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide

1: 72 percent / BuLi / tetrahydrofuran / 1.) -17 deg C, 1 h, 2.) -17 deg C, 2 h 2: 77 percent / conc. aq. HCl / ethanol / 3 h / Heating 3: 73 percent / acetic acid / 0.5 h / Heating View Scheme

1: O-MOM-sesamol With n-butyllithium; N,N,N',N,-tetramethylethylenediamine in hexane T=0°C; 2: methyl iodide in diethyl ether; hexane T=-78 - 20°C; Further stages.;

1.1: n-BuLi; B(OMe)3 / tetrahydrofuran 1.2: 95 percent / AcOH; H2O2 / 0 - 20 °C 2.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C 3.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 4.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 5.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 6.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 7.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 8.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 9.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 10.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 11.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 12.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 13.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 14.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 15.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 16.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 17.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 18.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 19.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 20.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 21.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 22.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 23.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 23.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 23.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 24.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 25.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme

1.1: BuLi / tetrahydrofuran / 0.5 h / 0 °C 1.2: 85 percent / tetrahydrofuran / 4 h / 20 °C 2.1: 91 percent / MCPBA / CHCl3 / 24 h / 20 °C 3.1: 59 percent / aq. NaOH / tetrahydrofuran / 4 h / 20 °C 4.1: 96 percent / K2CO3 / acetone / 48 h / 20 °C 5.1: 73 percent / NaI; HCl / acetone; methanol / 4 h View Scheme

1.1: BuLi; (MeO)3B / tetrahydrofuran 1.2: 92 percent / H2O2 2.1: 86 percent / TMSCl; NaI / acetonitrile View Scheme