acetic acid in tetrahydrofuran; water T=21°C; 7 h;

1: 92 percent / toluensulphonic acid / benzene / 4 h / Heating 2: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C -> -22 deg C, 2 h 3: 99 percent / pyridine / 40 h / 6 °C 4: chloramine-T / tetrahydrofuran / 1 h 5: 2,6-di-tert-butylpyridine, NaI / acetone / 17.5 h / 54 °C 6: 1.) LDA / 1.) DME, -78 deg C, 12 min, 2.) -78 deg C, 2 h 7: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min 8: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 9: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme

1: 80 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 2: 92 percent / toluensulphonic acid / benzene / 4 h / Heating 3: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C -> -22 deg C, 2 h 4: 99 percent / pyridine / 40 h / 6 °C 5: chloramine-T / tetrahydrofuran / 1 h 6: 2,6-di-tert-butylpyridine, NaI / acetone / 17.5 h / 54 °C 7: 1.) LDA / 1.) DME, -78 deg C, 12 min, 2.) -78 deg C, 2 h 8: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min 9: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 10: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme

1: 83 percent / LiAlH4 / tetrahydrofuran / 22 h / Heating 2: 80 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 3: 92 percent / toluensulphonic acid / benzene / 4 h / Heating 4: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C -> -22 deg C, 2 h 5: 99 percent / pyridine / 40 h / 6 °C 6: chloramine-T / tetrahydrofuran / 1 h 7: 2,6-di-tert-butylpyridine, NaI / acetone / 17.5 h / 54 °C 8: 1.) LDA / 1.) DME, -78 deg C, 12 min, 2.) -78 deg C, 2 h 9: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min 10: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 11: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme

1: 1.) LDA / 1.) DME, -78 deg C, 12 min, 2.) -78 deg C, 2 h 2: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min 3: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 4: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme

1: chloramine-T / tetrahydrofuran / 1 h 2: 2,6-di-tert-butylpyridine, NaI / acetone / 17.5 h / 54 °C 3: 1.) LDA / 1.) DME, -78 deg C, 12 min, 2.) -78 deg C, 2 h 4: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min 5: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 6: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme

1: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C -> -22 deg C, 2 h 2: 99 percent / pyridine / 40 h / 6 °C 3: chloramine-T / tetrahydrofuran / 1 h 4: 2,6-di-tert-butylpyridine, NaI / acetone / 17.5 h / 54 °C 5: 1.) LDA / 1.) DME, -78 deg C, 12 min, 2.) -78 deg C, 2 h 6: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min 7: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 8: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme

1: 99 percent / pyridine / 40 h / 6 °C 2: chloramine-T / tetrahydrofuran / 1 h 3: 2,6-di-tert-butylpyridine, NaI / acetone / 17.5 h / 54 °C 4: 1.) LDA / 1.) DME, -78 deg C, 12 min, 2.) -78 deg C, 2 h 5: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min 6: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 7: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme

1: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 2: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme

1: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min 2: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 3: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme