di-n-butylboryl trifluoromethanesulfonate in dichloromethane T=-78°C; 0.5 h;

diisobutylaluminium hydride in hexane T=-20 - 0°C; 1 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

indium 1.) DMF, 2.) DMF, 140 deg C, 4 h; Yield given. Multistep reaction;

1: lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h 2: diisobutylaluminium hydride / diethyl ether; hexane / 3 h / -78 °C View Scheme

n-butyllithium; cerium(III) chloride 1.) Et2O, RT, 1 h, 2.) Et2O, RT, 5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 - 20 °C 2.1: (R)-COP-Cl / dichloromethane / 24 h / 20 °C 3.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / |Reflux 4.1: sodium hydroxide / 12 h / 20 °C 5.1: 18 h / 20 °C 6.1: palladium 10 on activated carbon; tert.-butylhydroperoxide; potassium carbonate / dichloromethane; decane / 48 h / 40 °C 7.1: cerium(III) chloride heptahydrate / methanol / 0.5 h / 0 - 20 °C 7.2: 3 h / 0 °C View Scheme

1.1: Et3N / CH2Cl2 / 0 °C 2.1: LDA / tetrahydrofuran / 1 h / -78 - 0 °C 2.2: 3.6 g / CH2Cl2 / -78 - 20 °C View Scheme

1: With sodium hydride in diethyl ether T=0 - 20°C; 2: in xylene 12 h; Heating;