phospholipase D-P in chloroform T=45°C; 6 h; 250 mM CaCl2, 200 mM acetate buffer (pH 6.0);

1: 1.) trimethylsilyl chloride / 1.) pyridine, RT, 15 min, 2.) pyridine, RT, 2 h 2: 77 percent / 70percent HClO4 / 3 h / Ambient temperature 3: BaMnO4 / 1,2-dichloro-ethane / 3 h / Heating 4: 54 percent / CH2Cl2; hexane / 2 h / -75 °C 5: 1.) 90percent aq. HCOOH, 2.) NH4OH / 1.) 6 h, 2.) dioxane, RT, 6 h View Scheme

hydrogenchloride in methanol 18 h;

hydrogenchloride in methanol

boron trichloride in dichloromethane T=-78°C; 2 h;

methanol; trifluoroacetic acid in 1,2-dichloro-ethane T=20°C;

methanol; trifluoroacetic acid in 1,2-dichloro-ethane T=20°C;

1: chiral modular ligand; Et3N / Pd3dba3*CHCl3 / tetrahydrofuran / 5 h / 20 °C 2: 95 percent / PPh3; Et3N / Pd2dba3*CHCl3 / tetrahydrofuran / 12 h / 20 °C 3: 73 percent / MCPBA / CH2Cl2 / 44 h / 20 °C 4: 67 percent / DBU; ozone / tetrahydrofuran / 3 h / -78 - 20 °C 5: 62 percent / PPh3; DEAD / tetrahydrofuran / 6 h / 0 °C 6: 79 percent / DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 7: 89 percent / OsO4; NMO / acetone; H2O / 12 h / 20 °C 8: 71 percent / pyridine / 10 h / 20 °C 9: 71 percent / TsOH*H2O / 6 h / 20 °C 10: 61 percent / FeCl3*6H2O/SiO2 / CH2Cl2 / 15 h / 20 °C 11: 95 percent / pyridine / 10 h / 20 °C 12: 60 percent / DMF; SOCl2 / pyridine / 8 h / 20 °C 13: 73 percent / NH3 / methanol / 192 h / 20 °C 14: 91 percent / 1 M aq. HCl / 6 h / 80 °C View Scheme

1: chiral modular ligand; Et3N / Pd3dba3*CHCl3 / tetrahydrofuran / 5 h / 20 °C 2: 95 percent / PPh3; Et3N / Pd2dba3*CHCl3 / tetrahydrofuran / 12 h / 20 °C 3: 73 percent / MCPBA / CH2Cl2 / 44 h / 20 °C 4: 67 percent / DBU; ozone / tetrahydrofuran / 3 h / -78 - 20 °C 5: 62 percent / PPh3; DEAD / tetrahydrofuran / 6 h / 0 °C 6: 79 percent / DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 7: 89 percent / OsO4; NMO / acetone; H2O / 12 h / 20 °C 8: 71 percent / pyridine / 10 h / 20 °C 9: 71 percent / TsOH*H2O / 6 h / 20 °C 10: 61 percent / FeCl3*6H2O/SiO2 / CH2Cl2 / 15 h / 20 °C 11: 95 percent / pyridine / 10 h / 20 °C 12: 60 percent / DMF; SOCl2 / pyridine / 8 h / 20 °C 13: 73 percent / NH3 / methanol / 192 h / 20 °C 14: 91 percent / 1 M aq. HCl / 6 h / 80 °C View Scheme

1: 95 percent / PPh3; Et3N / Pd2dba3*CHCl3 / tetrahydrofuran / 12 h / 20 °C 2: 73 percent / MCPBA / CH2Cl2 / 44 h / 20 °C 3: 67 percent / DBU; ozone / tetrahydrofuran / 3 h / -78 - 20 °C 4: 62 percent / PPh3; DEAD / tetrahydrofuran / 6 h / 0 °C 5: 79 percent / DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 6: 89 percent / OsO4; NMO / acetone; H2O / 12 h / 20 °C 7: 71 percent / pyridine / 10 h / 20 °C 8: 71 percent / TsOH*H2O / 6 h / 20 °C 9: 61 percent / FeCl3*6H2O/SiO2 / CH2Cl2 / 15 h / 20 °C 10: 95 percent / pyridine / 10 h / 20 °C 11: 60 percent / DMF; SOCl2 / pyridine / 8 h / 20 °C 12: 73 percent / NH3 / methanol / 192 h / 20 °C 13: 91 percent / 1 M aq. HCl / 6 h / 80 °C View Scheme