1: PBr3 / diethyl ether / 3 h / 20 °C 2: dimethylformamide / 24 h / Ambient temperature 3: 78 percent / SeO2, t-BuOOH / CH2Cl2 / 25 h / 20 °C 4: 1.) Ti(OiPr)4, CaH2, 4A molecular sieves, D-(-)-DET, 2.) tert-BuOOH / 1.) CH2Cl2, -20 deg C, 15 min, 2.) CH2Cl2, toluene, -40 deg C, 5 h 5: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h 6: 78 percent / Li, EtNH2 / tetrahydrofuran / 4 h / -78 °C 7: 1.) Ph3P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h 8: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C 9: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C 10: Bu4N+F- / tetrahydrofuran / 24 h / 15 °C 11: 70 percent / Li, EtNH2 / tetrahydrofuran / 3.5 h / -78 °C 12: 49 percent / SOCl2, pyridine / 3 h / 15 °C 13: 92 percent / MnO2 / hexane / 12 h / 15 °C 14: 65 percent / 67 percent aq. Ca(ClO)2, glacial acetic acid / acetonitrile / 20 h / 15 °C View Scheme

1: PBr3 / diethyl ether / 3 h / 20 °C 2: dimethylformamide / 24 h / Ambient temperature 3: 78 percent / SeO2, t-BuOOH / CH2Cl2 / 25 h / 20 °C 4: 1.) Ti(OiPr)4, CaH2, 4A molecular sieves, D-(-)-DET, 2.) tert-BuOOH / 1.) CH2Cl2, -20 deg C, 15 min, 2.) CH2Cl2, toluene, -40 deg C, 5 h 5: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h 6: 78 percent / Li, EtNH2 / tetrahydrofuran / 4 h / -78 °C 7: 1.) Ph3P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h 8: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C 9: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C 10: Bu4N+F- / tetrahydrofuran / 24 h / 15 °C 11: 70 percent / Li, EtNH2 / tetrahydrofuran / 3.5 h / -78 °C 12: 49 percent / SOCl2, pyridine / 3 h / 15 °C 13: 92 percent / MnO2 / hexane / 12 h / 15 °C View Scheme

1,4-dioxane; trichloroacetic acid T=84°C; Schuetteln des Reaktionsprodukts in Aether und Petrolaether mit Ag2O und MgSO4;

1: 55 percent / H2 / Pd/C / ethanol / 21 h 2: 71 percent / iodine; triphenylphosphine; imidazole / toluene / 18 h View Scheme

1-fluoro-2-methyl-N,N-diisopropyl-propenylamine in chloroform T=20°C;

triethylamine in dichloromethane T=20°C; 48 h;

toluene-4-sulfonic acid in benzene T=20°C; 0.333333 h;

[(C6H6)(PCy3)(CO)RuH]+BF4- in chlorobenzene T=110°C; 8 h; Schlenk tube;

triethyl borane; sodium hydride; triphenylphosphine; palladium diacetate in tetrahydrofuran; hexane T=50°C; Alkylation; allylation; 20 h; Title compound not separated from byproducts;

n-butyllithium; triphenylborane; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine 1.) THF, r.t., 5 min; 2.) r.t., 10 min; 3.) THF, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;