Multi-step reaction with 11 steps
1: 95 percent / NaBH4, CeCl3 * 7 H2O / methanol / 1 h / -70 °C
2: 83 percent / NBS / tetrahydrofuran
3: 76 percent / Zn, NH4Cl / aq. ethanol / 5 h / Heating
4: hexane / 40 h / 30 °C / lipase MY
5: KOH / methanol
6: 1) O3, 2) Ph3P / 1) CH2Cl2, -70 deg C, 2) rt, overnight
7: 66 percent / KMnO4, MgSO4 / acetone; H2O / 5 h / 0 °C
8: 100 percent
9: 77 percent / 30percent acetic acid / 0.5 h / 60 °C
10: 84 percent / NaBH4, CeCl3 * 7H2O / methanol / 5 h / -10 °C
11: 91 percent / pyridine, DMAP / CH2Cl2 / Heating
With
pyridine; dmap; potassium hydroxide; sodium tetrahydroborate; potassium permanganate; N-Bromosuccinimide; cerium(III) chloride; magnesium sulfate; ammonium chloride; ozone; acetic acid; triphenylphosphine; zinc;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetone;