Multi-step reaction with 6 steps
1.1: biscyclopentadienylzirconium dichloride; lithium triethylborohydride / tetrahydrofuran / 2 h / 20 °C
1.2: 79 percent / I2 / tetrahydrofuran / 10 h / 20 °C
2.1: t-BuLi; CeCl3 / tetrahydrofuran; pentane / 1 h / -78 °C
2.2: 73 percent / tetrahydrofuran; pentane / 1 h / -78 °C
3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
3.2: tetrahydrofuran; hexane / 2 h / 0 - 20 °C
4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: CuCN / tetrahydrofuran; hexane / 0.5 h / -78 °C
4.3: 1.50 g / tetrahydrofuran; hexane / 4 h / -78 - 20 °C
5.1: O3; sudan III / CH2Cl2; methanol / -78 °C
5.2: NaBH4 / CH2Cl2; methanol / 17.5 h / 0 - 20 °C
6.1: 314 mg / Jones reagent / acetone / 0.25 h / 0 °C
With
n-butyllithium; jones reagent; cerium(III) chloride; zirconocene dichloride; oil scarlet; tert.-butyl lithium; lithium triethylborohydride; ozone;
In
tetrahydrofuran; methanol; hexane; dichloromethane; acetone; pentane;
DOI:10.1021/ol048936q