Multi-step reaction with 12 steps
1.1: TsOH / acetone; methanol / 2 h / 20 °C
1.2: 95 percent / NaBH4 / ethanol / 3 h / Heating
2.1: 86 percent / Et3N / CH2Cl2 / 0.08 h / -40 °C
3.1: 93 percent / K2CO3 / methanol / 2 h / 20 °C
4.1: 97 percent / CuI / tetrahydrofuran / 1 h / -40 °C
5.1: 98 percent / pyridine / CH2Cl2 / 0.17 h / -10 °C
6.1: NaN3 / dimethylformamide / 3 h / 20 °C
7.1: H2 / 10 percent Pd/C / ethyl acetate / 20 °C
8.1: 0.99 g / Et3N; Pb(NO3)2 / CH2Cl2 / 24 h / 20 °C
9.1: 95 percent / Dowex 50W-X8 resin / aq. methanol / 24 h / 20 °C
10.1: aq. NaIO4 / ethanol / 3 h / 20 °C
11.1: 2.65 g / NaBH4 / aq. ethanol / 0.17 h / 0 °C
12.1: 97 percent / Et3N / tetrahydrofuran / 0.17 h / 0 °C
With
pyridine; sodium tetrahydroborate; sodium periodate; copper(l) iodide; sodium azide; lead(II) nitrate; Dowex 50W-X8 resin; hydrogen; potassium carbonate; toluene-4-sulfonic acid; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;
4.1: Grignard reaction;