1.1: O3; O2 / cyclohexane; methanol / 5 °C 1.2: 53 percent / H2 / Pd/CaCO3/PbO 2.1: t-BuOK / tetrahydrofuran / 2.5 h / -40 - 25 °C 2.2: 57 percent / tetrahydrofuran / 2 h / -78 - 25 °C 3.1: 0.6 g / H2 / 10 percent Pd/C / ethanol / 72 h / 20 °C 4.1: Mg / tetrahydrofuran 4.2: 90 percent / tetrahydrofuran / 14 h / 0 - 20 °C View Scheme

1.1: O3; O2 / cyclohexane; methanol / 5 °C 1.2: 53 percent / H2 / Pd/CaCO3/PbO 2.1: t-BuOK / tetrahydrofuran / 2.5 h / -40 - 25 °C 2.2: 57 percent / tetrahydrofuran / 2 h / -78 - 25 °C 3.1: 0.6 g / H2 / 10 percent Pd/C / ethanol / 72 h / 20 °C View Scheme

1.1: O3; O2 / cyclohexane; methanol / 5 °C 1.2: 53 percent / H2 / Pd/CaCO3/PbO 2.1: t-BuOK / tetrahydrofuran / 2.5 h / -40 - 25 °C 2.2: 57 percent / tetrahydrofuran / 2 h / -78 - 25 °C 3.1: Mg / tetrahydrofuran 3.2: 90 percent / tetrahydrofuran / 14 h / 0 - 20 °C View Scheme

1.1: O3; O2 / cyclohexane; methanol / 5 °C 1.2: 53 percent / H2 / Pd/CaCO3/PbO 2.1: t-BuOK / tetrahydrofuran / 2.5 h / -40 - 25 °C 2.2: 57 percent / tetrahydrofuran / 2 h / -78 - 25 °C View Scheme

1: With oxygen; ozone in methanol; cyclohexane T=5°C; Oxidation; ozonolysis; 2: With hydrogen; Lindlar catalyst Reduction;

Yield given. Multistep reaction. Yields of byproduct given;