tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 2 h;

1.1: 100 percent / imidazole / tetrahydrofuran / 24 h / 20 °C 2.1: 90 percent / NaOMe; MeOH / 24 h / 20 °C 3.1: 81 percent / triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 18 h / 20 - 40 °C 4.1: 85 percent / NaOMe; MeOH / 24 h / 20 °C 5.1: 99 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C 6.1: NaH / tetrahydrofuran / 0 - 20 °C 6.2: 75 percent / tetrahydrofuran / 19 h / 75 °C 7.1: 74 percent / LiI / dimethylformamide / 17 h / 130 °C 8.1: 59 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: 99 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C 2.1: NaH / tetrahydrofuran / 0 - 20 °C 2.2: 75 percent / tetrahydrofuran / 19 h / 75 °C 3.1: 74 percent / LiI / dimethylformamide / 17 h / 130 °C 4.1: 59 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: 81 percent / triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 18 h / 20 - 40 °C 2.1: 85 percent / NaOMe; MeOH / 24 h / 20 °C 3.1: 99 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C 4.1: NaH / tetrahydrofuran / 0 - 20 °C 4.2: 75 percent / tetrahydrofuran / 19 h / 75 °C 5.1: 74 percent / LiI / dimethylformamide / 17 h / 130 °C 6.1: 59 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: 90 percent / NaOMe; MeOH / 24 h / 20 °C 2.1: 81 percent / triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 18 h / 20 - 40 °C 3.1: 85 percent / NaOMe; MeOH / 24 h / 20 °C 4.1: 99 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C 5.1: NaH / tetrahydrofuran / 0 - 20 °C 5.2: 75 percent / tetrahydrofuran / 19 h / 75 °C 6.1: 74 percent / LiI / dimethylformamide / 17 h / 130 °C 7.1: 59 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: 85 percent / NaOMe; MeOH / 24 h / 20 °C 2.1: 99 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C 3.1: NaH / tetrahydrofuran / 0 - 20 °C 3.2: 75 percent / tetrahydrofuran / 19 h / 75 °C 4.1: 74 percent / LiI / dimethylformamide / 17 h / 130 °C 5.1: 59 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: NaH / tetrahydrofuran / 0 - 20 °C 1.2: 75 percent / tetrahydrofuran / 19 h / 75 °C 2.1: 74 percent / LiI / dimethylformamide / 17 h / 130 °C 3.1: 59 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

1: 74 percent / LiI / dimethylformamide / 17 h / 130 °C 2: 59 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme