Multi-step reaction with 9 steps 1: 99 percent / DMSO, (COCl)2, Et3N / CH2Cl2 2: 96 percent / PPh3 / benzene / 80 °C3: 84 percent / n-BuLi / tetrahydrofuran / -78 °C4: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation5: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C6: 88 percent / H2 / Lindlar / methanol7: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature8: (C6H11)2NMgBr / methanol / -55 °C9: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86)  

Multi-step reaction with 6 steps 1: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation2: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C3: 88 percent / H2 / Lindlar / methanol4: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature5: (C6H11)2NMgBr / methanol / -55 °C6: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86)  

Multi-step reaction with 8 steps 1: 96 percent / PPh3 / benzene / 80 °C2: 84 percent / n-BuLi / tetrahydrofuran / -78 °C3: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation4: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C5: 88 percent / H2 / Lindlar / methanol6: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature7: (C6H11)2NMgBr / methanol / -55 °C8: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86)  

Multi-step reaction with 4 steps 1: 88 percent / H2 / Lindlar / methanol2: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature3: (C6H11)2NMgBr / methanol / -55 °C4: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86)  

Multi-step reaction with 10 steps 2: 99 percent / DMSO, (COCl)2, Et3N / CH2Cl2 3: 96 percent / PPh3 / benzene / 80 °C4: 84 percent / n-BuLi / tetrahydrofuran / -78 °C5: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation6: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C7: 88 percent / H2 / Lindlar / methanol8: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature9: (C6H11)2NMgBr / methanol / -55 °C10: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86)