1: 1.) Diisobutylaluminum hydride; 2.) 20percentH2SO4 / 1.) CH2Cl2, 0 deg C,benzene,15 min.; 45 min.at room temp.,2.) 30 min., 0 deg C 2: LDA 3: LDA 4: 100 percent / NaIO4 / OsO4 / H2O; 2-methyl-propan-2-ol / 30 h / Ambient temperature 5: 85 percent / Jones reagent / acetone 6: diethyl ether 7: 1.) NaNH2,bis(trimethylsilyl)amine 8: 1.) HCl; 2.) 2,4,5-collidine / 1.) CH2Cl2,-20 deg C; 2.) 180-185 deg C, 25 min. 9: 75 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / various solvent(s) / 2.5 h / 180 - 185 °C 10: LiAlH4 / diethyl ether / 2 h / 0 °C 11: 1.) Li, NH3; 2.) Jones reagent / 1.) Ether, -33 deg C; 2.) 0 deg C, 30 min View Scheme