1: 80 percent / H2O2; NaOH / methanol / 0.83 h / -40 °C 2: 91 percent / NaH / tetrahydrofuran / 1 h / 20 °C 3: 77 percent / NH3 / ethanol / 3 h / 20 °C 4: NaHCO3 / ethyl acetate; H2O / 20 °C 5: 77 percent / hydrogen / 10 percent Pd/C / ethanol 6: 27 percent / HCl / H2O / 45 °C View Scheme

1: 1.) copper(I) iodide, tributylphosphine; 2.) HMPA / 1.) THF, -78 deg C; 2.) -30 deg C, 3 h 2: 89 percent / aqu. HF, pyridine / acetonitrile 3: 98 percent / Al(Hg) / tetrahydrofuran; H2O 4: enzyme View Scheme

1.1: NaBH4; MeOH; CeCl3*7H2O / 23 °C 1.2: 73 percent / CH2Cl2 / 1 h / 0 °C 2.1: m-CPBA / CH2Cl2 / 0.25 h / 23 °C 2.2: 91 percent / triethylamine / CH2Cl2 / 17 h / 40 °C 3.1: 98 percent / Dess-Martin periodane / CH2Cl2 / 2 h / 23 °C 4.1: 85 percent / triethylamine / tetrahydrofuran / 3 h / 25 °C 5.1: 76 percent / Cs2CO3 / dioxane / 18 h / Heating 6.1: 75 percent / Cs2CO3 / acetonitrile / 20 h / 25 °C 7.1: AgOTf / CH2Cl2 / 1 h / 25 °C 7.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C 8.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C 9.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 10.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 11.1: 99 percent / HCl; methanol / 16 h / 25 °C 12.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 12.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 13.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 14.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 15.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 16.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

1: 84 percent / 5 M LiClO4 / diethyl ether / 24 h / Ambient temperature 2: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 10 min, 2) CH2Cl2, -78 deg C to r.t., 3 h 3: tetrahydrofuran / 3 h / -78 deg C to r.t. 4: 77 percent / Al/Hg / tetrahydrofuran; H2O / 96 h / Ambient temperature 5: 58 percent / Et3N, MsCl / CH2Cl2 / 10 h / Ambient temperature 6: 79 percent / <(Ph3P)CuH>6, H2O / benzene / 2 h / Ambient temperature View Scheme

1: 1.) copper(I) iodide, tributylphosphine; 2.) HMPA / 1.) THF, -78 deg C; 2.) -30 deg C, 3 h 2: 89 percent / aqu. HF, pyridine / acetonitrile 3: 98 percent / Al(Hg) / tetrahydrofuran; H2O View Scheme

1: With bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in dichloromethane T=20°C; 4 h; 2: With pyridinium chlorochromate in dichloromethane 12 h;

chromium(VI) oxide; sulfuric acid in acetone

manganese(IV) oxide in dichloromethane T=20°C;

1: methanephosphonic acid dimethyl ester With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.416667 h; 2: (1R,5S,8R)-8-methoxy-3,3-dimethyl-2,4,7-trioxabicyclo(3.3.0)octan-6-one in tetrahydrofuran; hexane T=-78 - 20°C; 3.75 h; Further stages.;

1: porcine pancreatic lipase 2: OsO4, N-methylmorpholine N-oxide 3: TsOH 4: H2 / Pd/C 5: 88 percent / pyridinium dichromate, 4 Angstroem molecular sieves / CH2Cl2 View Scheme