1: 95 percent / TPP / CCl4 / Ambient temperature; Irradiation 2: 80 percent / thiourea / methanol / Ambient temperature 3: HCl / methanol / 45 °C View Scheme

1: 81 percent / m-chloroperbenzoic acid / CH2Cl2 / 8 h / 0 °C 2: 90 percent / <(i-PrO)3P>4Pd / tetrahydrofuran; dimethylsulfoxide; hexane / 1) 0 deg C, 3 h, 2) rt, 16 h 3: 64 percent / methanol; dimethylsulfoxide / 16 h / 90 °C 4: 90 percent / dimethylaminopyridine, Et2NSF3 / CH2Cl2 / 1) -78 deg C to rt, 2 h, 2) rt, 22 h 5: 30percent aq. NH4OH / methanol / 12 h 6: 10 percent aq. HCl / 3 h View Scheme

1.1: chiral chloronitroso synthon / CH2Cl2 / 12 h / 0 °C 1.2: 85 percent / Al-Hg / acetonitrile; H2O / 1.5 h / 20 °C 2.1: Et3N / acetonitrile / 8 h / 25 °C 3.1: 3.78 g / DBU / acetonitrile / 9 h / 25 °C 4.1: NBS / H2O; acetone / 10 h / 20 °C 4.2: 88 percent / K2CO3 / acetonitrile / 4 h / 60 °C 5.1: SnCl4 / CH2Cl2 / 0.33 h / 25 °C 5.2: 98 percent / DMAP; K2CO3; pyridine / CH2Cl2 / 6 h / 25 °C 6.1: 78 percent / mercaptoacetic acid; LiOH / dimethylformamide / 1 h / 25 °C 7.1: acetonitrile / 4 h / 25 °C 8.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 9.1: 96 percent / DBU / benzene / 40 h / 70 °C 10.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 10.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

triethylamine in tetrahydrofuran 27 h; Heating;

1: 45 percent / thioxanthen-9-one / benzene / 0.67 h / Irradiation; ice-water cooling 2: 88 percent / acetic acid / H2O 3: 15 h / 55 °C 4: 0.45 g / N,N-diisopropylethylamine; trifluoromethanesulfonic anhydride / CH2Cl2 / 1.17 h / 0 °C View Scheme

1: 80 percent / ethyl acetate / 48 h / Heating 2: 95 percent / sodium dihydrogenphosphate; sodium amalgam / methanol 3: 80 percent / acetic acid; H2O / 2 h / 100 °C 4: 77 percent / triethylamine / CH2Cl2 / 2 h / 0 °C 5: 20.5 percent / sodium anthracenide / tetrahydrofuran View Scheme