Multi-step reaction with 9 steps
1.1: 97 percent / bromine / CHCl3; acetonitrile / 5.5 h / 20 °C
2.1: 95 percent / ethyldiisopropylamine / CH2Cl2; acetonitrile / 0 - 20 °C
3.1: 91 percent / LiAlH4 / tetrahydrofuran / 0 - 20 °C
4.1: 87 percent / imidazole; DMAP / CH2Cl2 / 0 - 20 °C
5.1: t-BuLi / tetrahydrofuran; pentane / 0.25 h / -78 °C
5.2: CuCN*2LiCl / tetrahydrofuran; pentane / 1 h / -15 °C
5.3: HMPA / tetrahydrofuran; pentane / -78 - 20 °C
6.1: 531 mg / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / 20 °C
7.1: 91 percent / IBX / dimethylsulfoxide / 5 h / 20 °C
8.1: BuLi / tetrahydrofuran / 0.25 h / -78 °C
8.2: 86 percent / tetrahydrofuran / -78 - 20 °C
9.1: 88 percent / Dess-Martin reagent / CH2Cl2 / 3 h / 20 °C
With
1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; bromine; tert.-butyl lithium; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; dichloromethane; chloroform; dimethyl sulfoxide; acetonitrile; pentane;
9.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(03)01136-0