1: ClSO3H, i-PrNO2 2: DIBAL / toluene / 1 h / -78 °C 3: 91.1 percent / TsCl, pyridine / 12 h / 35 °C 4: 1.) O3, 2.) NaBH4 / 1.) MeOH, -20 deg C, 2.) MeOH, from -20 deg C to RT 5: 98.6 percent / pyridine 6: 37 percent / H2O, tween 80, 0.1M phosphate buffer / CH2Cl2 / 24 h / 30 °C / lipase PS-30 (Amano) 7: TsCl, pyridine View Scheme

potassium hydroxide in ethanol

sodium hydroxide in ethanol 6 h; Heating;

1.1: copper(I) iodide; LDA / tetrahydrofuran; hexane / 2 h / -110 - -30 °C 1.2: 94 percent / tetrahydrofuran; hexane / 1 h / -30 °C 2.1: 96 percent / aq. NaOH / ethanol / 6 h / Heating View Scheme

1: 2.1 g / KOH / ethanol / 2 h / Heating 2: 1.78 g / pyridine / 5 h / Heating View Scheme

lithium aluminium tetrahydride in diethyl ether 3.5 h; Heating;