Multi-step reaction with 13 steps
1: 93 percent / LiAlH4 / tetrahydrofuran / 21 h / Heating
2: 88 percent / lead tetraacetate, pyridine / benzene / 3.5 h / 15 °C / Irradiation
3: 39 percent / boron trifluoride etherate / -20 deg C, 45 min, room temperature, 1 h
4: 65 percent / potassium hydroxide / methanol / 2.5 h / Heating
5: 94 percent / imidazole / dimethylformamide / 4 h / Ambient temperature
6: 87 percent / potassium hydride, 18-crown-6 / tetrahydrofuran / -78 - 20 °C
7: 1.) ozone, 2.) triphenylphosphine / 1.) dichloromethane, methanol, -70 deg C, 30 min, 2.) -70 deg C, 30 min
8: 76 percent / sodium borohydride / tetrahydrofuran; methanol / 0.58 h
9: 59 percent / pyridine / 4 h / 0 °C
10: 55 percent / n-butyl lithium / dioxane; hexane / 48 h / 90 °C
11: 62 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 3 h / 60 °C
12: 60 percent / pyridinium dichromate / CH2Cl2 / 18 h / Ambient temperature
13: 40 percent
With
pyridine; 1H-imidazole; lead(IV) acetate; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 18-crown-6 ether; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hydride; ozone; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0968-0896(98)00161-8