1: With oxalyl dichloride; dimethyl sulfoxide in chloroform T=-55°C; 3 h; Inert atmosphere; 2: With triethylamine in chloroform T=-55 - 0°C; 0.75 h;

hydrogen; trimethylacetic anhydride; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=80°C; P=22501.8 Torr; 24 h;

water T=20°C; Ring cleavage; acetalization; 16 h; Photolysis;

Pd-BaSO4; xylene Hydrogenation;

1.1: sulfuric acid / 17 h / 70 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / chloroform / 3 h / -55 °C / |Inert atmosphere 2.2: 0.75 h / -55 - 0 °C View Scheme

1.1: dihydrogen peroxide; acetic anhydride; maleic anhydride / chloroform; water / 16 h / 35 °C 2.1: sulfuric acid / 17 h / 70 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / chloroform / 3 h / -55 °C / |Inert atmosphere 3.2: 0.75 h / -55 - 0 °C View Scheme

sodium tetrahydroborate; Rhodium trichloride; formaldehyd; ethanol; α,ω-bis(diphenylphosphino)poy(ethylene glycol-400); hydrogen; silica gel in cyclohexane T=85°C; P=41371.8 Torr; 2 h; var. ratio substrate:catalyst, var. times; Product distribution;