1: 80 percent / pyridine 2: 59 percent / Bu3SnH; AIBN 3: 91 percent / DDQ 4: 97 percent / Bu4NF 5: Dess-Martin periodinane 6: 99 percent / Dess-Martin periodinane 7: 74 percent / n-BuLi 8: DIBAL-H 9: Dess-Martin periodinane 10: 67 percent / Li(i-Pr)2N / -78 °C 11: 79 percent / Cl2CHCO2H 12: Dess-Martin periodinane 13: NaClO2 14: MgBr2; n-BuSH; K2CO3 15: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 16: 91 percent / CF3CO2H / CH2Cl2 View Scheme

1: 59 percent / Bu3SnH; AIBN 2: 91 percent / DDQ 3: 97 percent / Bu4NF 4: Dess-Martin periodinane 5: 99 percent / Dess-Martin periodinane 6: 74 percent / n-BuLi 7: DIBAL-H 8: Dess-Martin periodinane 9: 67 percent / Li(i-Pr)2N / -78 °C 10: 79 percent / Cl2CHCO2H 11: Dess-Martin periodinane 12: NaClO2 13: MgBr2; n-BuSH; K2CO3 14: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 15: 91 percent / CF3CO2H / CH2Cl2 View Scheme

1: Dess-Martin periodinane 2: NaClO2 3: MgBr2; n-BuSH; K2CO3 4: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 5: 91 percent / CF3CO2H / CH2Cl2 View Scheme

1: 79 percent / Cl2CHCO2H 2: Dess-Martin periodinane 3: NaClO2 4: MgBr2; n-BuSH; K2CO3 5: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 6: 91 percent / CF3CO2H / CH2Cl2 View Scheme

1: 79 percent / Cl2CHCO2H 2: Dess-Martin periodinane 3: NaClO2 4: MgBr2; n-BuSH; K2CO3 5: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 6: 91 percent / CF3CO2H / CH2Cl2 View Scheme

1.1: pyridine / CH2Cl2 / 1 h / 0 °C 2.1: CH2Cl2 / 5 h / 20 °C 3.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 4.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 5.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 6.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 7.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 1.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 2.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 3.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 2.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 3.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 4.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C 2.1: 86 percent / 3 h / 160 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 4.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 4.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 5.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 6.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 6.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 7.1: pyridine / CH2Cl2 / 1 h / 0 °C 8.1: CH2Cl2 / 5 h / 20 °C 9.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 10.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 11.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 11.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 12.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 13.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 2.1: 76 percent / lithium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 4 h / 20 °C 3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 3.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 4.1: pyridine / CH2Cl2 / 1 h / 0 °C 5.1: CH2Cl2 / 5 h / 20 °C 6.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 7.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 8.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 9.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 10.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme