oxalyl dichloride; dimethyl sulfoxide

1.1: 83 percent / diisopropylamine; BuLi; HMPA / tetrahydrofuran; hexane / 1.3 h / -20 °C 2.1: Li; t-BuOH / tetrahydrofuran; aq. NH3 / -78 °C 3.1: aq. HF / acetonitrile; methanol / 3 h / 20 °C 3.2: 0.263 g / pyridine / 2 h / 20 °C 4.1: 45 percent / HMDS / CH2Cl2 / 1.5 h / 20 °C 5.1: 0.247 g / MgI2; HMDS / toluene / 2 h / 20 °C 6.1: RhCl3*H2O; K2CO3 / ethanol / 2 h / 60 °C 7.1: 94 percent / KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 8.1: O3 / CH2Cl2 / -78 °C 8.2: 35 percent / DIBALH / CH2Cl2 9.1: 85 percent / Pd(OAc)2; PPh3; Et3N / methanol; dimethylformamide / 3.5 h 10.1: 5.6 mg / DIBAL-H / diethyl ether; hexane / -78 - 20 °C 11.1: 55 percent / (COCl)2; DMSO View Scheme

1.1: Li; t-BuOH / tetrahydrofuran; aq. NH3 / -78 °C 2.1: aq. HF / acetonitrile; methanol / 3 h / 20 °C 2.2: 0.263 g / pyridine / 2 h / 20 °C 3.1: 45 percent / HMDS / CH2Cl2 / 1.5 h / 20 °C 4.1: 0.247 g / MgI2; HMDS / toluene / 2 h / 20 °C 5.1: RhCl3*H2O; K2CO3 / ethanol / 2 h / 60 °C 6.1: 94 percent / KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 7.1: O3 / CH2Cl2 / -78 °C 7.2: 35 percent / DIBALH / CH2Cl2 8.1: 85 percent / Pd(OAc)2; PPh3; Et3N / methanol; dimethylformamide / 3.5 h 9.1: 5.6 mg / DIBAL-H / diethyl ether; hexane / -78 - 20 °C 10.1: 55 percent / (COCl)2; DMSO View Scheme

1.1: aq. HF / acetonitrile; methanol / 3 h / 20 °C 1.2: 0.263 g / pyridine / 2 h / 20 °C 2.1: 45 percent / HMDS / CH2Cl2 / 1.5 h / 20 °C 3.1: 0.247 g / MgI2; HMDS / toluene / 2 h / 20 °C 4.1: RhCl3*H2O; K2CO3 / ethanol / 2 h / 60 °C 5.1: 94 percent / KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 6.1: O3 / CH2Cl2 / -78 °C 6.2: 35 percent / DIBALH / CH2Cl2 7.1: 85 percent / Pd(OAc)2; PPh3; Et3N / methanol; dimethylformamide / 3.5 h 8.1: 5.6 mg / DIBAL-H / diethyl ether; hexane / -78 - 20 °C 9.1: 55 percent / (COCl)2; DMSO View Scheme

1.1: 94 percent / KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 2.1: O3 / CH2Cl2 / -78 °C 2.2: 35 percent / DIBALH / CH2Cl2 3.1: 85 percent / Pd(OAc)2; PPh3; Et3N / methanol; dimethylformamide / 3.5 h 4.1: 5.6 mg / DIBAL-H / diethyl ether; hexane / -78 - 20 °C 5.1: 55 percent / (COCl)2; DMSO View Scheme

1.1: RhCl3*H2O; K2CO3 / ethanol / 2 h / 60 °C 2.1: 94 percent / KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 3.1: O3 / CH2Cl2 / -78 °C 3.2: 35 percent / DIBALH / CH2Cl2 4.1: 85 percent / Pd(OAc)2; PPh3; Et3N / methanol; dimethylformamide / 3.5 h 5.1: 5.6 mg / DIBAL-H / diethyl ether; hexane / -78 - 20 °C 6.1: 55 percent / (COCl)2; DMSO View Scheme

1.1: 45 percent / HMDS / CH2Cl2 / 1.5 h / 20 °C 2.1: 0.247 g / MgI2; HMDS / toluene / 2 h / 20 °C 3.1: RhCl3*H2O; K2CO3 / ethanol / 2 h / 60 °C 4.1: 94 percent / KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 5.1: O3 / CH2Cl2 / -78 °C 5.2: 35 percent / DIBALH / CH2Cl2 6.1: 85 percent / Pd(OAc)2; PPh3; Et3N / methanol; dimethylformamide / 3.5 h 7.1: 5.6 mg / DIBAL-H / diethyl ether; hexane / -78 - 20 °C 8.1: 55 percent / (COCl)2; DMSO View Scheme

1.1: O3 / CH2Cl2 / -78 °C 1.2: 35 percent / DIBALH / CH2Cl2 2.1: 85 percent / Pd(OAc)2; PPh3; Et3N / methanol; dimethylformamide / 3.5 h 3.1: 5.6 mg / DIBAL-H / diethyl ether; hexane / -78 - 20 °C 4.1: 55 percent / (COCl)2; DMSO View Scheme

1.1: 0.247 g / MgI2; HMDS / toluene / 2 h / 20 °C 2.1: RhCl3*H2O; K2CO3 / ethanol / 2 h / 60 °C 3.1: 94 percent / KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 4.1: O3 / CH2Cl2 / -78 °C 4.2: 35 percent / DIBALH / CH2Cl2 5.1: 85 percent / Pd(OAc)2; PPh3; Et3N / methanol; dimethylformamide / 3.5 h 6.1: 5.6 mg / DIBAL-H / diethyl ether; hexane / -78 - 20 °C 7.1: 55 percent / (COCl)2; DMSO View Scheme

1: 5.6 mg / DIBAL-H / diethyl ether; hexane / -78 - 20 °C 2: 55 percent / (COCl)2; DMSO View Scheme