1: 95 percent / pyridinium chlorochromate, NaOAc, molecular sieves / CH2Cl2 / 2 h / Ambient temperature 2: 30 percent / TiCl3(DME)1.5, Zn-Cu couple / 1,2-dimethoxy-ethane / Heating View Scheme

With  hydrogen; palladium on activated charcoal in  methanol; acetic acid; ethyl acetate P=2585.7 Torr; 48 h;