1.1: acetone / 16 h / Inert atmosphere; Reflux 2.1: sodium hydroxide / methanol / 12 h / Inert atmosphere; Reflux 2.2: pH 1 3.1: potassium carbonate / ethanol / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere 4.2: 0.5 h / -50 °C / Inert atmosphere 4.3: 20 °C View Scheme

1: 8.45 g / acetone / 3 h / Heating 2: aq. KOH / ethanol / 2 h / Heating 3: 3.56 g / K2CO3 / acetone / 2.5 h / Heating 4: 96 percent / oxalic acid dihydrate / aq. methanol / 2.5 h / Heating View Scheme

1.1: 79 percent / K2CO3 / acetone / 3 h / Heating 2.1: 98 percent / PdCl2(PPh3)2; CuI; Et3N / dimethylformamide / 6 h / 100 °C 3.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3.2: 99 percent / H2O / tetrahydrofuran / 20 °C 4.1: 96 percent / CuI; PdCl2(PPh3)2; iPr2NH / dimethylformamide / 1 h / 60 °C 5.1: 98 percent / I2 / CH2Cl2 / 12 h / 25 °C 6.1: 60 percent / PdCl2(PPh3)2; K2CO3 / dimethylformamide / 6 h / 60 °C 7.1: 99 percent / n-Bu4N(1+)*F(1-) / dimethylformamide / 2 h / 100 °C View Scheme

1: acetone / 16 h / Heating 2: 86 percent / KOH / ethanol; H2O / 2 h / 90 °C View Scheme

potassium carbonate in acetone 3 h; Heating;

1.1: acetone / 16 h / Inert atmosphere; Reflux 2.1: sodium hydroxide / methanol / 12 h / Inert atmosphere; Reflux 2.2: pH 1 3.1: potassium carbonate / ethanol / 16 h / Inert atmosphere; Reflux View Scheme

1: 15.0 g / acetone / 3 h / Heating 2: 94 percent / KI; CuI / hexamethylphosphoric acid triamide / 3 h / 150 °C 3: 98 percent / CuI; Et3N / PdCl2(PPh3)2 / dimethylformamide / 1 h / 20 °C 4: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C 5: 96 percent / CuI; i-Pr2NH / PdCl2(PPh3)2 / dimethylformamide / 1.5 h / 60 °C 6: 81 percent / DIBAL-H / toluene; CH2Cl2 / 3 h / -78 °C 7: 67 percent / TBAF / tetrahydrofuran / 3 h / Heating 8: 78 percent / NaOMe / methanol / 20 h / Heating View Scheme