sodium hydroxide in ethanol 14 h; Heating;

1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 7: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 8: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 9: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 10: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme

1: 11 percent / Cu / 1 h / 210 °C 2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 3: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 4: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 5: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 6: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 7: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 8: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme

1: 11 percent / Cu / 1 h / 210 °C 2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 3: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 4: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 5: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 6: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 7: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 8: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme

1: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 3: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 4: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 5: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 6: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 7: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 8: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme

1: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 2: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 3: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 4: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 5: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 6: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 7: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme

1: thionyl chloride / 1 h / 25 °C 2: tetrahydrofuran / 2 h / 20 °C 3: 88 percent / 4.5 N aq. HCl / 12 h / Heating 4: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 5: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 6: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 7: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 8: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 9: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 10: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 11: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme

1: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 2: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 3: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 4: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 5: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 6: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme

1: 88 percent / 4.5 N aq. HCl / 12 h / Heating 2: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 3: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 4: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 5: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 6: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 7: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 8: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 9: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme

1: 95 percent / thionyl chloride / 18 h / 20 °C 2: CH2Cl2 / 2 h / 20 °C 3: thionyl chloride / 1 h / 25 °C 4: tetrahydrofuran / 2 h / 20 °C 5: 88 percent / 4.5 N aq. HCl / 12 h / Heating 6: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 7: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 8: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 9: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 10: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 11: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 12: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 13: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme