1.1: 16.4 g / Zn; PPh3 / CH2Cl2 / 2 h 2.1: n-BuLi / tetrahydrofuran; hexane / 1.67 h / -78 - 23 °C 2.2: 100 percent / tetrahydrofuran; hexane / 8 h / 20 °C 3.1: 99.6 percent / TBAF / tetrahydrofuran / 5 h / 20 °C 4.1: Dess-Martin reagent / CH2Cl2 5.1: Sn(OTf); Et3N / CH2Cl2 / 1 h / -20 °C 5.2: 2.82 g / CH2Cl2 / 1 h / -78 °C 6.1: 75.0 mg / NaBH(OAc)3; AcOH / 3 h / 5 °C 7.1: 90 percent / DBU / CH2Cl2 / 2 h / 20 °C 8.1: tributyltin hydride; Pd(OAc)2; PCy3 / tetrahydrofuran; hexane 8.2: 769 mg / I2 / CH2Cl2 / 0.33 h 9.1: 433 mg / aq. K3PO4; PdCl2(dppf)*CH2Cl2 / diethyl ether; tetrahydrofuran; dimethylformamide / 18 h 10.1: DIBAL-H / toluene / 2 h / -78 °C 11.1: 361 mg / pyridine / 8 h / 20 °C 12.1: 91 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C 13.1: 42 percent / SnCl4; molecular sieves 4A / CHCl3; CH2Cl2 / 14 h / -5 - 20 °C 14.1: 87 percent / NaOMe / methanol / 15 h / 25 °C 15.1: 98 percent / Et3N / CH2Cl2 16.1: 62 percent / IBX / dimethylformamide / 36 h 17.1: 50 percent / aq. HF / acetonitrile / 20 °C View Scheme