1: 1.) O3; 2.) Zn,50percentHOAc / 1.) CH2Cl2,- 78 deg C; 2.) reflux 2: 79 percent / Jones reagent / acetone 3: 95 percent / K2CO3 / acetone / 2 h / Heating 4: 97 percent / Br2 / acetic acid; acetic acid / 6.5 h 5: 91 percent / CaCO3 / N,N-dimethyl-acetamide / 0.75 h / Heating 6: 95 percent / KOH / H2O; ethanol / 15.5 h / Ambient temperature 7: 1.) Diisobutylaluminum hydride; 2.) 20percentH2SO4 / 1.) CH2Cl2, 0 deg C,benzene,15 min.; 45 min.at room temp.,2.) 30 min., 0 deg C 8: LDA 9: LDA 10: 100 percent / NaIO4 / OsO4 / H2O; 2-methyl-propan-2-ol / 30 h / Ambient temperature 11: 85 percent / Jones reagent / acetone 12: diethyl ether 13: 1.) NaNH2,bis(trimethylsilyl)amine 14: 1.) HCl; 2.) 2,4,5-collidine / 1.) CH2Cl2,-20 deg C; 2.) 180-185 deg C, 25 min. 15: 75 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / various solvent(s) / 2.5 h / 180 - 185 °C 16: LiAlH4 / diethyl ether / 2 h / 0 °C 17: 1.) Li, NH3; 2.) Jones reagent / 1.) Ether, -33 deg C; 2.) 0 deg C, 30 min View Scheme