1: 1.) NaH; 2.) LDA / 1.) THF; 2.) THF, -78 deg C, 15 min. 2: 90 percent / NaOMe / ethanol / 19 h / Heating 3: 1.) Et3N, CH3SO2Cl; 2.) LiAlH4 / 1.) THF, -23 deg C, 1 h; 2.) ether, room temp., 2 h 4: HBr / pentane / 0.17 h 5: TiCl4 / CH2Cl2 / 0.5 h, -20 deg C, 10 h, room temp. View Scheme

phosphoric acid T=140°C;

1: 95 percent / NaOH 2: 90 percent / AlCl3 3: 1.) NaH; 2.) LDA / 1.) THF; 2.) THF, -78 deg C, 15 min. 4: 90 percent / NaOMe / ethanol / 19 h / Heating 5: 1.) Et3N, CH3SO2Cl; 2.) LiAlH4 / 1.) THF, -23 deg C, 1 h; 2.) ether, room temp., 2 h 6: HBr / pentane / 0.17 h 7: TiCl4 / CH2Cl2 / 0.5 h, -20 deg C, 10 h, room temp. View Scheme

1: 90 percent / AlCl3 2: 1.) NaH; 2.) LDA / 1.) THF; 2.) THF, -78 deg C, 15 min. 3: 90 percent / NaOMe / ethanol / 19 h / Heating 4: 1.) Et3N, CH3SO2Cl; 2.) LiAlH4 / 1.) THF, -23 deg C, 1 h; 2.) ether, room temp., 2 h 5: HBr / pentane / 0.17 h 6: TiCl4 / CH2Cl2 / 0.5 h, -20 deg C, 10 h, room temp. View Scheme

titanium tetrachloride in dichloromethane 0.5 h, -20 deg C, 10 h, room temp.; Yield given;

hydrogen bromide; titanium tetrachloride Yield given. Multistep reaction;

1: concentrated sulfuric acid / 160 °C 2: sodium; amyl alcohol 3: aqueous phosphoric acid / 140 °C View Scheme

1: sodium; amyl alcohol 2: aqueous phosphoric acid / 140 °C View Scheme