1: diethyl ether / 0 °C 2: 2.) conc. HCl / 1.) ether, reflux 2.) acetone, room temperature 3: 93 percent / PCC / CH2Cl2 / Ambient temperature 4: 97 percent / p-TSA / benzene / Heating 5: 48 percent / O3 / methanol; CH2Cl2 / -78 °C 6: 1.) Mg / 1.) Et2O, reflux 2.) Et2O, 0 deg C 7: 88 percent / PCC / CH2Cl2 / Ambient temperature 8: 58 percent / O3 / methanol; CH2Cl2 / -78 °C 9: 1.) NaH / 1.) Et2O, 0 deg C to 10 deg C 2.) Et2O, 0 deg C to room temperature 10: 1.) HS(CH2)3SH, BF3*Et2O, 2.) CuO/CuCl2 / 1.) CH2Cl2, 0 deg C, 2.) H2O-acetone, reflux 11: 1.) (C6H11)2NMgBr / 1.) THF, -50 deg C, 2.) 0 deg C 12: 1.) NaOMe, 2.) Zn/AcOH, conc. HCl / 1.) CH2Cl2, MeOH, room temperature 2.) THF, room temperature 13: LiSPr / hexamethylphosphoric acid triamide / Ambient temperature View Scheme