1.1: 87 percent / NaH / dimethylformamide / 6 h / 20 °C 2.1: O3; O2; MeOH / CH2Cl2 / 0 °C 2.2: 95 percent / NaBH4 / CH2Cl2 / 3 h / 20 °C 3.1: NaNO2; H2SO4 / H2O / 0 °C 4.1: 0.02 g / benzene / 1.5 h / 27 °C / UV-irradiation 5.1: 80 percent / pyridine / cooling 6.1: 75 percent / LiAlH4 / various solvent(s) / 0 - 20 °C 7.1: NaNO2; H2SO4 / H2O / 0 °C 8.1: 0.02 g / benzene / 1.5 h / 27 °C / UV-irradiation View Scheme

1: (7R,9Z)-octadec-9-en-7-ol With ozone in methanol T=0°C; 2: methanol With hydroxylamine hydrochloride 10 h; Heating; Further stages.;

1.1: 87 percent / NaH / dimethylformamide / 6 h / 20 °C 2.1: O3; O2; MeOH / CH2Cl2 / 0 °C 2.2: 95 percent / NaBH4 / CH2Cl2 / 3 h / 20 °C 3.1: NaNO2; H2SO4 / H2O / 0 °C 4.1: 0.02 g / benzene / 1.5 h / 27 °C / UV-irradiation View Scheme