1: 1.) 1,2-dimethoxyethane , Ethanol heat for 14.5 h; 2.) 15 min,0 deg C 2: 1.) O3; 2.) Zn,50percentHOAc / 1.) CH2Cl2,- 78 deg C; 2.) reflux 3: 79 percent / Jones reagent / acetone 4: 95 percent / K2CO3 / acetone / 2 h / Heating 5: 97 percent / Br2 / acetic acid; acetic acid / 6.5 h 6: 91 percent / CaCO3 / N,N-dimethyl-acetamide / 0.75 h / Heating 7: 95 percent / KOH / H2O; ethanol / 15.5 h / Ambient temperature 8: 1.) Diisobutylaluminum hydride; 2.) 20percentH2SO4 / 1.) CH2Cl2, 0 deg C,benzene,15 min.; 45 min.at room temp.,2.) 30 min., 0 deg C 9: LDA 10: LDA 11: 100 percent / NaIO4 / OsO4 / H2O; 2-methyl-propan-2-ol / 30 h / Ambient temperature 12: 85 percent / Jones reagent / acetone 13: diethyl ether 14: 1.) NaNH2,bis(trimethylsilyl)amine 15: 1.) HCl; 2.) 2,4,5-collidine / 1.) CH2Cl2,-20 deg C; 2.) 180-185 deg C, 25 min. 16: 75 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / various solvent(s) / 2.5 h / 180 - 185 °C 17: LiAlH4 / diethyl ether / 2 h / 0 °C 18: 1.) Li, NH3; 2.) Jones reagent / 1.) Ether, -33 deg C; 2.) 0 deg C, 30 min View Scheme

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

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

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

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

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

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

1: 95 percent / KOH / H2O; ethanol / 15.5 h / Ambient temperature 2: 1.) Diisobutylaluminum hydride; 2.) 20percentH2SO4 / 1.) CH2Cl2, 0 deg C,benzene,15 min.; 45 min.at room temp.,2.) 30 min., 0 deg C 3: LDA 4: LDA 5: 100 percent / NaIO4 / OsO4 / H2O; 2-methyl-propan-2-ol / 30 h / Ambient temperature 6: 85 percent / Jones reagent / acetone 7: diethyl ether 8: 1.) NaNH2,bis(trimethylsilyl)amine 9: 1.) HCl; 2.) 2,4,5-collidine / 1.) CH2Cl2,-20 deg C; 2.) 180-185 deg C, 25 min. 10: 75 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / various solvent(s) / 2.5 h / 180 - 185 °C 11: LiAlH4 / diethyl ether / 2 h / 0 °C 12: 1.) Li, NH3; 2.) Jones reagent / 1.) Ether, -33 deg C; 2.) 0 deg C, 30 min View Scheme

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

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