1: TiCl3, NH4OAc / 1,2-dimethoxy-ethane; H2O / 10 h / Ambient temperature 2: 1) NaBH4 2) 9percent HCl / 1) MeOH, r.t., 40 min 2) reflux, 1h 3: 391 mg / Jones reagent / acetone; propan-2-ol; H2O / 0 °C 4: 1 percent / DIBAH / diethyl ether / -78 °C 5: p-TsOH / diethyl ether / 40 h / Heating 6: 2) 20percent NaOH / 1) HOAc, reflux, 6 d 2) MeOH, r.t., 30 min 7: 53 percent / CrO3, pyridine / 2 h / Ambient temperature 8: 1) LiAlH4 2) CrO3, pyridine / 1) ether, reflux, 2 h 2) r.t., 30 min View Scheme

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