1: 96 percent / 30percent NaOH, / methanol / 1.5 h / Heating 2: 98 percent / H2, / PtO2, / methanol / 40 °C / 2574.3 Torr View Scheme

sodium hydroxide in methanol 1.5 h; Heating;

1: 96 percent / 30percent NaOH, / methanol / 1.5 h / Heating 2: 98 percent / H2, / PtO2, / methanol / 40 °C / 2574.3 Torr 3: 1.) NaH, 2.) n-BuLi, / 1.) THF, 70 to 75 deg C, 2 h, 2.) THF, hexane, -70 deg C, 30 min, 3.) THF, hexane, 5 to 10 deg C, overnight, 4: 1.) SOCl2, 2.) K2CO3, / 1.) CH2Cl2, 0 to 10 deg C, 1.5 h, 2.) DMF, RT; 18 h, 5: 60 percent / 80percent m-CPBA, / CH2Cl2 / 0.5 h View Scheme

Multi-step reaction with 4 steps 1: 96 percent / 30percent NaOH, / methanol / 1.5 h / Heating2: 98 percent / H2, / PtO2, / methanol / 40 °C / 2574.3 Torr3: 1.) NaH, 2.) n-BuLi, / 1.) THF, 70 to 75 deg C, 2 h, 2.) THF, hexane, -70 deg C, 30 min, 3.) THF, hexane, 5 to 10 deg C, overnight,4: 1.) SOCl2, 2.) K2CO3, / 1.) CH2Cl2, 0 to 10 deg C, 1.5 h, 2.) DMF, RT; 18 h,  

With  formic acid; sodium cyanoborohydride in  tetrahydrofuran 3 h;  Ambient temperature;