Multi-step reaction with 9 steps
1.1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 0.75 h / Heating
1.2: CuCN / tetrahydrofuran / -40 - 0 °C
1.3: tetrahydrofuran / 3 h / -10 - 0 °C
2.1: KF / methanol / 1 h / 20 °C
3.1: 93 percent / imidazole; DMAP / dimethylformamide / 3 h / 20 °C
4.1: 70 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / -30 °C
5.1: NaH / tetrahydrofuran; various solvent(s) / 2 h / 50 °C
5.2: 93 percent / tetrahydrofuran / 5 h
6.1: 90 percent / AIBN; n-Bu3SnH / toluene / 0.5 h / 90 °C
7.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
8.1: 97 percent / triethylamine / CH2Cl2 / 0.08 h / 0 °C
9.1: 80 percent / lithium aluminum hydride / diethyl ether / 8 h / Heating
With
1H-imidazole; dmap; potassium fluoride; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; magnesium; ethylene dibromide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
6.1: Barton radical deoxygenation;
DOI:10.1016/j.tet.2006.10.067