1: With ozone in methanol; dichloromethane T=-78°C; Oxidation; 2: With dimethylsulfide in methanol; dichloromethane Hydrolysis;

1.1: 88 percent / xylene / 48 h / 75 °C 2.1: 55 percent / H2 / Raney Ni / ethanol / 4 h / 2068.59 Torr 3.1: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 4.1: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 5.1: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 6.1: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C 7.1: ozone / methanol; CH2Cl2 / -78 °C 7.2: 47 percent / dimethyl sulfide / methanol; CH2Cl2 View Scheme

1.1: 55 percent / H2 / Raney Ni / ethanol / 4 h / 2068.59 Torr 2.1: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 3.1: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 4.1: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 5.1: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C 6.1: ozone / methanol; CH2Cl2 / -78 °C 6.2: 47 percent / dimethyl sulfide / methanol; CH2Cl2 View Scheme

1.1: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 2.1: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 3.1: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 4.1: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C 5.1: ozone / methanol; CH2Cl2 / -78 °C 5.2: 47 percent / dimethyl sulfide / methanol; CH2Cl2 View Scheme

1.1: thionyl chloride / 4 h / Heating 2.1: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 3.1: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 4.1: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 5.1: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C 6.1: ozone / methanol; CH2Cl2 / -78 °C 6.2: 47 percent / dimethyl sulfide / methanol; CH2Cl2 View Scheme

1.1: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 2.1: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 3.1: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 4.1: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C 5.1: ozone / methanol; CH2Cl2 / -78 °C 5.2: 47 percent / dimethyl sulfide / methanol; CH2Cl2 View Scheme

1.1: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 2.1: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 3.1: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C 4.1: ozone / methanol; CH2Cl2 / -78 °C 4.2: 47 percent / dimethyl sulfide / methanol; CH2Cl2 View Scheme

1.1: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C 2.1: ozone / methanol; CH2Cl2 / -78 °C 2.2: 47 percent / dimethyl sulfide / methanol; CH2Cl2 View Scheme

1.1: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 2.1: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C 3.1: ozone / methanol; CH2Cl2 / -78 °C 3.2: 47 percent / dimethyl sulfide / methanol; CH2Cl2 View Scheme

1: 1.) SOCl2 / 1.) CH2Cl2, RT, 3.5 h, 2.) DMSO; a.) from 50 deg C to 60 deg C, 4 d, b.) RT, 18 d 2: 33 percent / 1.) KO-t-Bu, 2.) 30percent aq. oxalic acid / 1.) THF, DMSO, -10 deg C, 1 h, 2.) THF, reflux, 1 h View Scheme