1: 93 percent / MCPBA / CH2Cl2 / 0 °C 2: diethyl ether / 0 °C 3: 2.) conc. HCl / 1.) ether, reflux 2.) acetone, room temperature 4: 93 percent / PCC / CH2Cl2 / Ambient temperature 5: 97 percent / p-TSA / benzene / Heating 6: 48 percent / O3 / methanol; CH2Cl2 / -78 °C 7: 1.) Mg / 1.) Et2O, reflux 2.) Et2O, 0 deg C 8: 88 percent / PCC / CH2Cl2 / Ambient temperature 9: 58 percent / O3 / methanol; CH2Cl2 / -78 °C 10: 1.) NaH / 1.) Et2O, 0 deg C to 10 deg C 2.) Et2O, 0 deg C to room temperature 11: 1.) HS(CH2)3SH, BF3*Et2O, 2.) CuO/CuCl2 / 1.) CH2Cl2, 0 deg C, 2.) H2O-acetone, reflux 12: 1.) (C6H11)2NMgBr / 1.) THF, -50 deg C, 2.) 0 deg C 13: 1.) NaOMe, 2.) Zn/AcOH, conc. HCl / 1.) CH2Cl2, MeOH, room temperature 2.) THF, room temperature 14: LiSPr / hexamethylphosphoric acid triamide / Ambient temperature View Scheme