sodium hydroxide; ozone in methanol; dichloromethane T=-78°C;

sodium hydroxide; ozone in dichloromethane T=-78°C;

2: ethanol / 4 h / 110 °C 3: 1) catecholborane, 2) NaOAc*3H2O / 1) CHCl3, -10 deg C, 1 h, 2) 1 h, reflux 4: Me3SiI / CHCl3 / 1 h / 25 °C View Scheme

1: 10-undecenyl alcohol With t-butyl ammonium iodide in tetrahydrofuran T=0 - 20°C; 2: benzyl bromide in tetrahydrofuran T=20°C; 3.5 h;

t-DDT; diMe-Imd-BH3; t-BuON=NOt-Bu in benzene T=80°C; 2 h;

1: phosphorus tribromide / dichloromethane / 1 h / 0 °C 2: diMe-Imd-BH3; t-DDT; t-BuON=NOt-Bu / benzene / 2 h / 80 °C View Scheme

1.1: sodium hydride / tetrahydrofuran / 2 h / Reflux 1.2: 20 °C 2.1: tetrabutylammomium bromide; sodium acetate; pyridinium chlorochromate / dichloromethane / 2 h / 20 °C / Molecular sieve 3.1: magnesium / diethyl ether / 2.5 h / 20 °C 3.2: 3 h / -78 - 0 °C 4.1: phosphorus tribromide / dichloromethane / 1 h / 0 °C 5.1: diMe-Imd-BH3; t-DDT; t-BuON=NOt-Bu / benzene / 2 h / 80 °C View Scheme

1.1: tetrabutylammomium bromide; sodium acetate; pyridinium chlorochromate / dichloromethane / 2 h / 20 °C / Molecular sieve 2.1: magnesium / diethyl ether / 2.5 h / 20 °C 2.2: 3 h / -78 - 0 °C 3.1: phosphorus tribromide / dichloromethane / 1 h / 0 °C 4.1: diMe-Imd-BH3; t-DDT; t-BuON=NOt-Bu / benzene / 2 h / 80 °C View Scheme

1.1: magnesium / diethyl ether / 2.5 h / 20 °C 1.2: 3 h / -78 - 0 °C 2.1: phosphorus tribromide / dichloromethane / 1 h / 0 °C 3.1: diMe-Imd-BH3; t-DDT; t-BuON=NOt-Bu / benzene / 2 h / 80 °C View Scheme

1.1: sodium hydride / tetrahydrofuran / 2 h / Reflux 1.2: 20 °C 2.1: tetrabutylammomium bromide; sodium acetate; pyridinium chlorochromate / dichloromethane / 2 h / 20 °C / Molecular sieve 3.1: magnesium / diethyl ether / 2.5 h / 20 °C 3.2: 3 h / -78 - 0 °C 4.1: phosphorus tribromide / dichloromethane / 1 h / 0 °C 5.1: diMe-Imd-BH3; t-DDT; t-BuON=NOt-Bu / benzene / 2 h / 80 °C View Scheme