0.0833333 h; microwave irradiation;

tri-n-butyl-tin hydride in methanol T=20°C; Elimination; reduction; 3 h; Photolysis; Title compound not separated from byproducts;

1.1: 100 percent / pyridine / 1 h / 0 - 20 °C 2.1: 100 percent / pyridine / 2 h / 0 - 20 °C 3.1: 100 percent / p-toluenesulfonic acid; EtOH / 1 h / 0 - 20 °C 4.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 72 h / 0 - 20 °C 5.1: CeCl3 / tetrahydrofuran / 4 h / -78 °C 5.2: 82 percent / tetrahydrofuran / 3 h / -78 °C 6.1: 82 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 7.1: 99 percent / AlCl3 / diethyl ether / 1 h / 0 - 20 °C 8.1: 97 percent / pyridine / 0 - 20 °C 9.1: ozone / CH2Cl2 / 1 h / -78 °C 9.2: 69 percent / Me2S / CH2Cl2 / 1 h / -78 - 20 °C 10.1: 91 percent / KMnO4; phosphate buffer / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C / pH 7 11.1: NEt3; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C 11.2: 72 percent / NEt3 / tetrahydrofuran / 0.5 h / 0 °C 12.1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C 13.1: 84 percent Spectr. / Bu3SnH / methanol / 3 h / 20 °C / Photolysis View Scheme

1.1: 99 percent / AlCl3 / diethyl ether / 1 h / 0 - 20 °C 2.1: 97 percent / pyridine / 0 - 20 °C 3.1: ozone / CH2Cl2 / 1 h / -78 °C 3.2: 69 percent / Me2S / CH2Cl2 / 1 h / -78 - 20 °C 4.1: 91 percent / KMnO4; phosphate buffer / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C / pH 7 5.1: NEt3; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C 5.2: 72 percent / NEt3 / tetrahydrofuran / 0.5 h / 0 °C 6.1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C 7.1: 84 percent Spectr. / Bu3SnH / methanol / 3 h / 20 °C / Photolysis View Scheme

1.1: 97 percent / pyridine / 0 - 20 °C 2.1: ozone / CH2Cl2 / 1 h / -78 °C 2.2: 69 percent / Me2S / CH2Cl2 / 1 h / -78 - 20 °C 3.1: 91 percent / KMnO4; phosphate buffer / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C / pH 7 4.1: NEt3; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C 4.2: 72 percent / NEt3 / tetrahydrofuran / 0.5 h / 0 °C 5.1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C 6.1: 84 percent Spectr. / Bu3SnH / methanol / 3 h / 20 °C / Photolysis View Scheme

1.1: 91 percent / KMnO4; phosphate buffer / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C / pH 7 2.1: NEt3; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C 2.2: 72 percent / NEt3 / tetrahydrofuran / 0.5 h / 0 °C 3.1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C 4.1: 84 percent Spectr. / Bu3SnH / methanol / 3 h / 20 °C / Photolysis View Scheme

1.1: ozone / CH2Cl2 / 1 h / -78 °C 1.2: 69 percent / Me2S / CH2Cl2 / 1 h / -78 - 20 °C 2.1: 91 percent / KMnO4; phosphate buffer / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C / pH 7 3.1: NEt3; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C 3.2: 72 percent / NEt3 / tetrahydrofuran / 0.5 h / 0 °C 4.1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C 5.1: 84 percent Spectr. / Bu3SnH / methanol / 3 h / 20 °C / Photolysis View Scheme

1.1: NEt3; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C 1.2: 72 percent / NEt3 / tetrahydrofuran / 0.5 h / 0 °C 2.1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C 3.1: 84 percent Spectr. / Bu3SnH / methanol / 3 h / 20 °C / Photolysis View Scheme

1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C 2: 84 percent Spectr. / Bu3SnH / methanol / 3 h / 20 °C / Photolysis View Scheme

1.1: 82 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 2.1: 99 percent / AlCl3 / diethyl ether / 1 h / 0 - 20 °C 3.1: 97 percent / pyridine / 0 - 20 °C 4.1: ozone / CH2Cl2 / 1 h / -78 °C 4.2: 69 percent / Me2S / CH2Cl2 / 1 h / -78 - 20 °C 5.1: 91 percent / KMnO4; phosphate buffer / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C / pH 7 6.1: NEt3; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C 6.2: 72 percent / NEt3 / tetrahydrofuran / 0.5 h / 0 °C 7.1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C 8.1: 84 percent Spectr. / Bu3SnH / methanol / 3 h / 20 °C / Photolysis View Scheme