phosphorous acid trimethyl ester in dichloromethane T=20°C; 0.166667 h;

potassium carbonate in methanol; water Ambient temperature;

1: With soybean lipoxygenase; oxygen 2: With sodium tetrahydroborate Further stages.;

1: diethyl ether 2: 2) Et2NH, CuI / 1) Pd(PPh3)4 / 1) benzene, rt, 1 h, 2) 5 h 3: 91 percent / H2 / Lindlar catalyst / ethanol 4: 92 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature 5: 73 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

1: 2) Et2NH, CuI / 1) Pd(PPh3)4 / 1) benzene, rt, 1 h, 2) 5 h 2: 91 percent / H2 / Lindlar catalyst / ethanol 3: 92 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature 4: 73 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

1: Jones' reagent / acetone / 2 h / 0 °C 2: diethyl ether 3: 2) Et2NH, CuI / 1) Pd(PPh3)4 / 1) benzene, rt, 1 h, 2) 5 h 4: 91 percent / H2 / Lindlar catalyst / ethanol 5: 92 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature 6: 73 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

1: 82 percent / (+)-DIPT, t-BuO2H, Ti(O-iPr)4 2: 88 percent / CCl4, PPh3 3: 79 percent 4: 78 percent / imidazole / dimethylformamide 5: 2) Et2NH, CuI / 1) Pd(PPh3)4 / 1) benzene, rt, 1 h, 2) 5 h 6: 91 percent / H2 / Lindlar catalyst / ethanol 7: 92 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature 8: 73 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

1: 88 percent / CCl4, PPh3 2: 79 percent 3: 78 percent / imidazole / dimethylformamide 4: 2) Et2NH, CuI / 1) Pd(PPh3)4 / 1) benzene, rt, 1 h, 2) 5 h 5: 91 percent / H2 / Lindlar catalyst / ethanol 6: 92 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature 7: 73 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

1: 78 percent / imidazole / dimethylformamide 2: 2) Et2NH, CuI / 1) Pd(PPh3)4 / 1) benzene, rt, 1 h, 2) 5 h 3: 91 percent / H2 / Lindlar catalyst / ethanol 4: 92 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature 5: 73 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

1: 79 percent 2: 78 percent / imidazole / dimethylformamide 3: 2) Et2NH, CuI / 1) Pd(PPh3)4 / 1) benzene, rt, 1 h, 2) 5 h 4: 91 percent / H2 / Lindlar catalyst / ethanol 5: 92 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature 6: 73 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme