Multi-step reaction with 9 steps
1.1: tert-butyllithium / tetrahydrofuran; pentane / 0.42 h / -78 - -42 °C
1.2: tetrahydrofuran; pentane / -78 - 20 °C
2.1: NaI / acetone / 48 h / Heating
3.1: n-butyllithium / tetrahydrofuran; hexane / 0 - 20 °C
3.2: HMPA / tetrahydrofuran; hexane / 48 h / 20 °C
4.1: 1.38 g / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
5.1: CHCl3 / 2 h / Irradiation
6.1: m-chloroperbenzoic acid / CHCl3 / 0.33 h
7.1: 2.70 g / MgSO4 / benzene / 1 h / Heating
8.1: 79 percent / potassium carbonate; DMAP / dimethylformamide; H2O / 48 h / 20 °C
9.1: 95 percent / triethylamine / Pd(OAc)2 / 48 h / 70 °C / 20520 Torr
With
dmap; n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; magnesium sulfate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide;
palladium diacetate;
In
tetrahydrofuran; hexane; chloroform; water; N,N-dimethyl-formamide; acetone; pentane; benzene;
DOI:10.1021/jo026595t