1: diethyl ether; tetrahydrofuran / Ambient temperature 2: OsO4/NaIO4 / tetrahydrofuran; H2O / Ambient temperature 3: benzene / Ambient temperature 4: H2 / Pd-C / ethanol / 1551.4 Torr / Ambient temperature 5: conc. HCl / 0 °C 6: H2SO4, CuSO / Ambient temperature 7: 1.) BF3*Et2O, HgO (red) 2.) NaBH4 / 1.) THF, r.t. 2.) EtOH, r.t. 8: Ph3P, CCl4 / Heating 9: LiOH / H2O; 1,2-dimethoxy-ethane / Ambient temperature 10: LDA / tetrahydrofuran / -25 °C 11: NaH / tetrahydrofuran / Ambient temperature 12: 1.5 N HCl / H2O; tetrahydrofuran / Ambient temperature 13: diethyl ether 14: benzene / Ambient temperature 15: CuCl, TMEDA, O2 / acetone / 0.02 h / Ambient temperature 16: DDQ / H2O; CH2Cl2 / Ambient temperature 17: n-Bu4NF / tetrahydrofuran; acetic acid View Scheme

1: 67 percent / PdCl2(dppf) / tetrahydrofuran / 30 °C 2: 1.) 9-BBN; 2.) H2O2, NaOH / THF View Scheme

2: CrO3, H2SO4 View Scheme

1: With ethylmagnesium bromide 2: With dilithium tetrachlorocuprate

0.5 h;

in tetrahydrofuran T=-10 - 20°C; 18 h;

water in tetrahydrofuran 1 h; Ambient temperature; Product distribution;