1: 88 percent / NaNH2 / diethyl ether / 3 h / 6 °C 2: 73 percent / H2, AcOH / 5percent Pt/C / 1 h / 120 °C / 112509 Torr View Scheme

1: 88 percent / NaNH2 / diethyl ether / 3 h / 6 °C 2: 73 percent / H2, AcOH / 5percent Pt/C / 1 h / 120 °C / 112509 Torr View Scheme

dibenzo-18-crown-6 in benzene 2.5 h; Ambient temperature;

1: 90 percent / KF, 18-crown-6 2: 2.)H2SO4 / 1. and 2. MeOH 3: 60 percent / aq. HCl / acetone / Heating 4: 1.) DBN 2.) pyrrolidine, HOAc 5: 59 percent / BF3*Et2O / CH2Cl2 / 0 °C 6: diisobutylaluminum hydride (DIBAL) / toluene / -78 °C 7: 53 percent / sodium cyanoborohydride (NaCNBH3) / 2-methyl-propan-2-ol 8: N-chlorosuccinimide, AgNO3 / acetonitrile View Scheme

1: Mg / methanol / 20 °C 2: BBr3 / CH2Cl2 / 20 °C View Scheme

CuF(PPh3)3*2MeOH; bis[2-(diphenylphosphino)phenyl] ether; tert-butyl alcohol in toluene T=25°C; 3.5 h; Inert atmosphere; chemoselective reaction;

cesium fluoride in toluene; acetonitrile T=75°C; Diels-Alder reaction; 48 h;

cesium fluoride in toluene; acetonitrile T=75°C; Diels-Alder reaction; 48 h;

boron tribromide