1: 1.) NaBH4; 2.) 9percent HCl / 2.) reflux 2: CrO3/H2SO4 / acetone 3: diisobutylaluminum hydride (DIBAH) / diethyl ether 4: p-TsOH / Heating 5: 1.) AcOH; 2.) NaOH / 1.) reflux; 2.) MeOH 6: 53 percent / CrO3/pyridine 7: LiAlH4 / diethyl ether 8: CrO3/pyridine View Scheme

With  titanium(III) chloride; ammonium acetate in  ethylene glycol dimethyl ether; water 10 h;  Ambient temperature;