18-crown-6 ether; silver(I) in N,N-dimethyl acetamide T=100°C; P=760.051 Torr; 15 h; Molecular sieve;

chromium(VI) oxide; periodic acid in acetonitrile 1 h;

oxygen; mercury(II) trifluoroacetate in tetrahydrofuran 72 h; Ambient temperature;

sodium tetrahydroborate in tetrahydrofuran 0.666667 h; Ambient temperature;

1: 5 percent / NaOEt / ethanol; tetrahydrofuran / 5 h / 0 °C 2: 67 percent / NaH; LiBH4 / dioxane; tetrahydrofuran; various solvent(s) / 28 h / Heating View Scheme

1.1: NaH / tetrahydrofuran; various solvent(s) / 0.33 h / 0 - 20 °C 1.2: n-BuLi / tetrahydrofuran; hexane; various solvent(s) / 0.5 h / -78 °C 1.3: 78 percent / tetrahydrofuran; hexane; various solvent(s) / 0.67 h / -78 °C 2.1: 75 percent / pyridinium chlorochromate; Al2O3 / CH2Cl2 / 0.5 h / 20 °C 3.1: 5 percent / NaOEt / ethanol; tetrahydrofuran / 5 h / 0 °C 4.1: 67 percent / NaH; LiBH4 / dioxane; tetrahydrofuran; various solvent(s) / 28 h / Heating View Scheme

1: 75 percent / pyridinium chlorochromate; Al2O3 / CH2Cl2 / 0.5 h / 20 °C 2: 5 percent / NaOEt / ethanol; tetrahydrofuran / 5 h / 0 °C 3: 67 percent / NaH; LiBH4 / dioxane; tetrahydrofuran; various solvent(s) / 28 h / Heating View Scheme

1.1: 77 percent / N-bromosuccinimide; AIBN / benzene / 1 h / Heating 2.1: AcOH; K2CO3 / dimethylformamide / 2 h / 20 °C 2.2: 94 percent / KOH / dimethylformamide; methanol; H2O / 2 h / 20 °C 3.1: 86 percent / SmI2; HMPA / tetrahydrofuran / 2 h / 20 °C 4.1: 79 percent / Ag2CO3-Celite / benzene / 1.5 h / Heating View Scheme

1: 86 percent / SmI2; HMPA / tetrahydrofuran / 2 h / 20 °C 2: 79 percent / Ag2CO3-Celite / benzene / 1.5 h / Heating View Scheme

1.1: AcOH; K2CO3 / dimethylformamide / 2 h / 20 °C 1.2: 94 percent / KOH / dimethylformamide; methanol; H2O / 2 h / 20 °C 2.1: 86 percent / SmI2; HMPA / tetrahydrofuran / 2 h / 20 °C 3.1: 79 percent / Ag2CO3-Celite / benzene / 1.5 h / Heating View Scheme