1: 1.) Mg, 2.) Li2CuCl4 / 1.) ether, THF, 2.) THF, -78 to -55 deg C, 1 h 2: aq. concd. HCl / methanol / 48 h / 20 °C 3: 1.) HBr, 2.) KOH / 1.) glacial acetic acid, 0 deg C, 5 min, 2.) methanol, 15 min View Scheme

potassium hydroxide in methanol 2 h; Ambient temperature; Yield given;

1: 1.) diisobutylaluminium hydride / 1.) n-hexane, toluene, 50 deg C, 4 h, 2.) + THF, room temperature, overnight 2: 75 percent / silver nitrate, silver oxide, 4 Angstroem molecular sieves / tetrahydrofuran / 9 h / 30 °C 3: TBHP, Ti(O-i-Pr)4, diisopropyl L-tartrate, 4 Angstroem molecular sieves / CH2Cl2; 2,2,4-trimethyl-pentane / 44 h / -20 °C 4: tetraethylammonium fluoride hydrate / acetonitrile / 6 h / 60 °C View Scheme

1: 75 percent / silver nitrate, silver oxide, 4 Angstroem molecular sieves / tetrahydrofuran / 9 h / 30 °C 2: TBHP, Ti(O-i-Pr)4, diisopropyl L-tartrate, 4 Angstroem molecular sieves / CH2Cl2; 2,2,4-trimethyl-pentane / 44 h / -20 °C 3: tetraethylammonium fluoride hydrate / acetonitrile / 6 h / 60 °C View Scheme

1: TBHP, Ti(O-i-Pr)4, diisopropyl L-tartrate, 4 Angstroem molecular sieves / CH2Cl2; 2,2,4-trimethyl-pentane / 44 h / -20 °C 2: tetraethylammonium fluoride hydrate / acetonitrile / 6 h / 60 °C View Scheme

sodium hydroxide; trimethyl-oxonium tetrafluoroborate 1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h; Yield given. Multistep reaction;

cytochrome P450 variant RH-47 (mutation BM-3); NADPH in phosphate buffer; ethanol T=20°C; pH=8; 3 h; Product distribution; Further Variations:Reagents;