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

diisobutylaluminium hydride; pyridinium chlorochromate 1.) 1.) hexane, -20 deg C to 0 deg C, 1 h, 2.) methylene chloride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1.1: diisobutylaluminium hydride / diethyl ether; hexane / 3 h / -78 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 - 20 °C 3.1: (R)-COP-Cl / dichloromethane / 24 h / 20 °C 4.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / |Reflux 5.1: sodium hydroxide / 12 h / 20 °C 6.1: 18 h / 20 °C 7.1: palladium 10 on activated carbon; tert.-butylhydroperoxide; potassium carbonate / dichloromethane; decane / 48 h / 40 °C 8.1: cerium(III) chloride heptahydrate / methanol / 0.5 h / 0 - 20 °C 8.2: 3 h / 0 °C View Scheme

1.1: 97 percent / DIBAL-H / CH2Cl2 / 3 h / -78 °C 2.1: Et3N / CH2Cl2 / 0 °C 3.1: LDA / tetrahydrofuran / 1 h / -78 - 0 °C 3.2: 3.6 g / CH2Cl2 / -78 - 20 °C View Scheme

diisobutylaluminium hydride in dichloromethane T=-78°C; 3 h;

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