1: With ozone in methanol; dichloromethane T=-78°C; 2: With dimethylsulfide in methanol; dichloromethane T=-78 - 20°C; 16 h;

Celite; isopropyl alcohol; pyridinium chlorochromate in dichloromethane T=20°C; 1 h;

boron trifluoride diethyl etherate 0.116667 h; Ambient temperaturemicrowave irradiation;

1.1: Cs2CO3 / dimethylformamide / 1 h / 70 °C 2.1: chlorobenzene / 24 h / Heating 3.1: 94 percent / Et3N / CH2Cl2 / 18 h / 0 - 20 °C 4.1: 84 percent / LiCl / [PdCl2{p(C6H5)3}2] / dimethylformamide / 2 h / 110 °C 5.1: 91 percent / RhCl3 / ethanol / 0.5 h / Heating 6.1: NaHMDS; O2; P(OEt)3 / tetrahydrofuran / 2 h / -78 °C 6.2: pyridinium dichromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 0 °C 7.1: 73 percent / p-toluenesulfonic acid monohydrate / toluene / 20 h / Heating 8.1: O3 / methanol; CH2Cl2 / -78 °C 8.2: 60 percent / Me2S / CH2Cl2; methanol / 16 h / -78 - 20 °C View Scheme

1.1: 91 percent / RhCl3 / ethanol / 0.5 h / Heating 2.1: NaHMDS; O2; P(OEt)3 / tetrahydrofuran / 2 h / -78 °C 2.2: pyridinium dichromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 0 °C 3.1: 73 percent / p-toluenesulfonic acid monohydrate / toluene / 20 h / Heating 4.1: O3 / methanol; CH2Cl2 / -78 °C 4.2: 60 percent / Me2S / CH2Cl2; methanol / 16 h / -78 - 20 °C View Scheme

1.1: chlorobenzene / 24 h / Heating 2.1: 94 percent / Et3N / CH2Cl2 / 18 h / 0 - 20 °C 3.1: 84 percent / LiCl / [PdCl2{p(C6H5)3}2] / dimethylformamide / 2 h / 110 °C 4.1: 91 percent / RhCl3 / ethanol / 0.5 h / Heating 5.1: NaHMDS; O2; P(OEt)3 / tetrahydrofuran / 2 h / -78 °C 5.2: pyridinium dichromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 0 °C 6.1: 73 percent / p-toluenesulfonic acid monohydrate / toluene / 20 h / Heating 7.1: O3 / methanol; CH2Cl2 / -78 °C 7.2: 60 percent / Me2S / CH2Cl2; methanol / 16 h / -78 - 20 °C View Scheme

1.1: 94 percent / Et3N / CH2Cl2 / 18 h / 0 - 20 °C 2.1: 84 percent / LiCl / [PdCl2{p(C6H5)3}2] / dimethylformamide / 2 h / 110 °C 3.1: 91 percent / RhCl3 / ethanol / 0.5 h / Heating 4.1: NaHMDS; O2; P(OEt)3 / tetrahydrofuran / 2 h / -78 °C 4.2: pyridinium dichromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 0 °C 5.1: 73 percent / p-toluenesulfonic acid monohydrate / toluene / 20 h / Heating 6.1: O3 / methanol; CH2Cl2 / -78 °C 6.2: 60 percent / Me2S / CH2Cl2; methanol / 16 h / -78 - 20 °C View Scheme

1.1: 84 percent / LiCl / [PdCl2{p(C6H5)3}2] / dimethylformamide / 2 h / 110 °C 2.1: 91 percent / RhCl3 / ethanol / 0.5 h / Heating 3.1: NaHMDS; O2; P(OEt)3 / tetrahydrofuran / 2 h / -78 °C 3.2: pyridinium dichromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 0 °C 4.1: 73 percent / p-toluenesulfonic acid monohydrate / toluene / 20 h / Heating 5.1: O3 / methanol; CH2Cl2 / -78 °C 5.2: 60 percent / Me2S / CH2Cl2; methanol / 16 h / -78 - 20 °C View Scheme

boron tribromide in dichloromethane T=-78 - 25°C; 24 h;

1: 91 percent / aq. NH4OH / 120 h / 20 °C 2: 82 percent / MgSO4 / diethyl ether / 10 h / 20 °C 3: 84 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 4: 85 percent / Bu3SnH; AIBN / benzene / 4 h / Heating 5: NaBH4 / ethanol / 0.5 h / 20 °C 6: 415.1 mg / EDC / CH2Cl2 / 16 h / 20 °C 7: 98 percent / MCPBA / CH2Cl2 / 0.5 h / 0 °C 8: 63 percent / CaCO3 / toluene / 13 h / Heating 9: methanol / 1.5 h / 20 °C / Irradiation 10: 2.8 mg / Pd/C / acetic acid / 3 h / 80 °C View Scheme