1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / 30 - 35 °C / |Inert atmosphere 2.1: manganese(IV) oxide / ethanol / 3 h / 20 - 60 °C / |Inert atmosphere; |Reflux 3.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / -30 °C / |Inert atmosphere 3.2: 1 h / -75 - -65 °C / |Inert atmosphere 4.1: carbon / 0.5 h / |Reflux View Scheme

1: lithium aluminium tetrahydride / diethyl ether / -78 - 20 °C 2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve 3: lithium diisopropyl amide / tetrahydrofuran / -78 °C 4: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); isopropylamine / 3.5 h 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C 6: zinc / water; isopropyl alcohol / 26 h / 40 °C View Scheme

1: lithium aluminium tetrahydride / diethyl ether / -78 - 20 °C 2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve 3: lithium diisopropyl amide / tetrahydrofuran / -78 °C 4: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); isopropylamine / 3.5 h 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C View Scheme

1: With lithium aluminium tetrahydride in diethyl ether T=-78 - 20°C; 3 h; 2: With water in diethyl ether

1: lithium aluminium tetrahydride / diethyl ether / -78 - 20 °C 2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve 3: lithium diisopropyl amide / tetrahydrofuran / -78 °C 4: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); isopropylamine / 3.5 h View Scheme

1: (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate With lithium aluminium tetrahydride in diethyl ether T=0°C; 0.5 h; 2: triphenylphosphine hydrobromide in methanol T=20°C; 24 h;

1: LiAlH4 / diethyl ether / 0.25 h / Ambient temperature 2: methanol / 17 h / Ambient temperature View Scheme