1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) from -78 deg C to RT, overnight 2: 90 percent / m-chloroperbenzoic acid / CHCl3 / 24 h / 25 °C View Scheme

1: 75 percent / n-BuLi / tetrahydrofuran; hexane / 6 h / -78 - 20 °C 2: 78 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

(i) nBuLi, (ii) H2, Pd-C, (iii) aq. HCl; Multistep reaction;

1: n-BuLi / tetrahydrofuran / 4 h / -78 - 20 °C 2: H2 / PtO2 / benzene; ethanol / 4 h / Ambient temperature 3: BF3*Et2O, EtSH / CH2Cl2 / 6 h / 0 °C 4: 98 percent 5: 75 percent / BBr3 / -20 °C 6: Cr(ClO4)2, ethylenediamine / dimethylformamide / 0.33 h / 0 °C View Scheme