Multi-step reaction with 11 steps
1.1: 84 percent / (+)-Ipc2BCl / tetrahydrofuran / 12 h / -35 °C
2.1: 90 percent / n-BuLi / diethyl ether; tetrahydrofuran / 2.5 h / -78 - 20 °C
3.1: 85 percent / IBr / toluene; CH2Cl2 / 1 h / -85 °C
4.1: 96 percent / K2CO3 / methanol / 2 h / 20 °C
5.1: 96 percent / Et3N; DMAP / dimethylformamide / 3 h / 20 °C
6.1: 91 percent / CuI / diethyl ether / 0.5 h / -40 °C
7.1: 88 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
8.1: 83 percent / dimethylformamide; H2O / 20 h / 60 °C
9.1: 95 percent / Et3N / CH2Cl2 / 6 h / 20 °C
10.1: Cy2BH / CH2Cl2 / 6 h / 0 - 20 °C
10.2: 90 percent / H2O2; NaOH / H2O / 1 h / 0 - 20 °C
11.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / 0 °C
With
dmap; copper(l) iodide; n-butyllithium; (+)-β-chlorodiisopinocampheylborane; bis(cyclohexanyl)borane; iodine(I) bromide; potassium carbonate; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(01)02105-0