hydrogen; palladium on activated charcoal in ethanol Ambient temperature;

tetrafluoroboric acid; mercury(II) oxide 1) THF, -20 deg C, 30 min, 2) 80 deg C, 5 h; Multistep reaction;

1: H2, Wilkinson catalyst 2: O3 / ethanol / -78 °C 3: NaBH4 / tetrahydrofuran; ethanol 4: imidazole / dimethylformamide 5: Br2 / CCl4 6: 67 percent / Li2CO3, LiBr / dimethylformamide 7: tetrahydrofuran 8: LiN(iPr)2 / tetrahydrofuran 9: LiCl, methanesulfonyl chloride / dimethylformamide 10: K2CO3, CuI, Bu4NBr / dimethylformamide 11: 90 percent / H2 / Lindlar catalyst 12: 83 percent / Bu4NF, H2O / tetrahydrofuran 13: Dess-Martin periodinane, NaOAc / CH2Cl2 14: TiCl3*DME1.5, Zn-Cu / 1,2-dimethoxy-ethane / 36 h / 0 °C 15: 1.) MsCl, pyridine 2.) Bu4NOH / 1.) ether; 2.) THF 16: LiN(iPr)2 / tetrahydrofuran 17: 84 percent / Dess-Martin periodinane View Scheme

1: 66 percent / m-CPBA, NaHCO3 / CH2Cl2 / 0.5 h / 0 °C 2: 1) O3, 2) Me2S / 1) methanol, -65 - -70 deg C; 2) -78 deg C to r.t., 4 h 3: 82 percent / m-CPBA / CH2Cl2 / 60 h 4: 87 percent / zinc powder, NaI, sodium acetate, acetic acid / CH2Cl2 / 4 h / Ambient temperature 5: 88 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 6: 49 percent / pyridine / a) 0 deg C, 1.5 h; b) r.t., 6 h 7: NaN3 / dimethylformamide 8: LiAlH4 / diethyl ether 9: 70 percent / pyridine / CH2Cl2 / a) 0 deg C, 0.5 h; b) r.t., 8 h 10: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 11: 1) N,N-carbonyldiimidazole / 1) THF, r.t., 1 h; 2) r.t., 10 h 12: 93 percent / LiAlH4 / diethyl ether / 6 h / Heating View Scheme

1.1: n-BuLi; TMEDA / tetrahydrofuran / 24 h / 23 °C 1.2: O2 / tetrahydrofuran 2.1: imidazole / dimethylformamide 3.1: O3 / CH2Cl2 / -78 °C 3.2: Me2S / CH2Cl2 4.1: n-BuLi / tetrahydrofuran / -78 °C 5.1: DIBALH / CH2Cl2 / -78 °C 6.1: imidazole / dimethylformamide 7.1: MgBr2 / diethyl ether / 20 °C 8.1: TiCl4; Zn; pyridine / 1,2-dimethoxy-ethane / Heating 9.1: PPTs / ethanol / 20 °C 10.1: Ti(i-PrO)4; L-(+)-DET; t-BuOOH / CH2Cl2 / -20 °C 11.1: I2; Ph3P; imidazole / diethyl ether; acetonitrile / 0 °C 12.1: NaBH3(CN) / tetrahydrofuran; hexamethylphosphoric acid triamide / 60 °C 13.1: TBAF / tetrahydrofuran View Scheme

1: With silica gel Isomerization; 2 h; Heating; 2: With peracetic acid T=-20°C; Epoxidation;

benzoic acid methyl ester; trifluorormethanesulfonic acid in ethyl acetate 72 h; UV-irradiation;

rat P450 2C11 enzyme in phosphate buffer T=37°C; pH=7.4; 0.5 h; Enzyme kinetics;