1: DIBAL-H / tetrahydrofuran / 3 h / -78 °C 2: 80 percent / CCl4, PPh3 / 18 h / Heating 3: 92 percent / LiEt3BH / tetrahydrofuran / 1 h / -78 °C 4: 95 percent / CSA / methanol / 1 h / 25 °C 5: SO3*Py, DMSO, Et3N / tetrahydrofuran / 1 h / 0 °C 6: LDA / tetrahydrofuran / 1.) -78 to -40 deg C, 1 h, 2.) -78 deg C, 2 min View Scheme

1.1: 97 percent / benzene / 8 h / Heating 2.1: 10.95 g / LiHMDS / tetrahydrofuran / 0.67 h / 55 °C 3.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C 4.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 4.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 5.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 6.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 7.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 7.2: 93 percent / tetrahydrofuran / 1 h / -78 °C 8.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 9.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 10.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 11.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 11.2: tetrahydrofuran / 1.5 h / -95 - -80 °C View Scheme

1.1: 99 percent / imidazole / dimethylformamide / 3 h / 0 - 20 °C 2.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 2.2: 93 percent / tetrahydrofuran / 1 h / -78 °C 3.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 4.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 5.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 6.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 6.2: tetrahydrofuran / 1.5 h / -95 - -80 °C View Scheme

1.1: 99 percent / Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 0 °C 2.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 2.2: tetrahydrofuran / 1.5 h / -95 - -80 °C View Scheme

1.1: 88 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 2.1: 99 percent / imidazole / dimethylformamide / 3 h / 0 - 20 °C 3.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 3.2: 93 percent / tetrahydrofuran / 1 h / -78 °C 4.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 5.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 6.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 7.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 7.2: tetrahydrofuran / 1.5 h / -95 - -80 °C View Scheme

1: 77 percent / Et3N 2: LDA View Scheme

1: 77 percent / Et3N 2: LDA View Scheme

2,6-dimethylpyridine in dichloromethane T=0°C; 3 h;

2,6-dimethylpyridine in dichloromethane T=0°C; 3 h; Yield given;

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