1.1: CrO3; aq. sulfuric acid / acetone / 1 h / 0 °C 2.1: toluene / 16 h / 20 - 60 °C 3.1: 90 percent / diisobutylaluminum hydride / CH2Cl2 / 0.5 h / -15 °C 4.1: NaH / diethyl ether / 0.25 h / -15 - 20 °C 4.2: diethyl ether / 2.3 h / -15 - 20 °C 5.1: 160 mg / toluene / 89 h / 140 °C 6.1: 72 percent / trifluoroacetic acid / H2O / 5 h / 0 °C 7.1: sodium periodate / methanol; H2O / 28 h / 0 - 20 °C 8.1: Jones reagent / acetone / 22 h / 0 - 5 °C 9.1: 1.34 g / NaBH4 / methanol / 3 h / 0 - 20 °C 10.1: 92 percent / 2,6-lutidine / CH2Cl2 / 43 h / 0 - 20 °C 11.1: 75 percent / sodium / liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C 12.1: pyridine; trifluoroacetic acid; N,N'-dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 5 h / 20 °C 13.1: 41 mg / tetrahydrofuran / 13.75 h / -15 - 20 °C 14.1: 78 percent / pyridine; trifluoroacetic acid; N,N'-dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 7 h / 20 °C 15.1: 70 percent / triisobutylaluminum / hexane; 1,2-dichloro-ethane / 3.8 h / 0 - 20 °C 16.1: aq. trifluoroacetic acid / 17 h / 20 - 50 °C 16.2: 76 percent / sodium methoxide / methanol / 3 h / 0 °C 17.1: ozone / methanol / 0.08 h / -78 °C 17.2: dimethyl sulfide / methanol / 5 h / -78 - 20 °C 18.1: 27 mg / HOSO2NH2; NaH2PO4*2H2O; NaClO2 / 2-methyl-propan-2-ol; H2O / 0.25 h View Scheme

Multi-step reaction with 6 steps 1: 89 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 24 h / Ambient temperature2: 85 percent / tetrahydrofuran / Ambient temperature3: 1) H2, 5 percent Rh-Al2O3; 2) H2, 10 percent Pd-C / 1) EtOH, 8-10 deg C; 2) EtOH, r.t., 6 h4: 89 percent / NaH / dimethylsulfoxide / 20 h / Ambient temperature5: 83 percent / aq. HCl / tetrahydrofuran / 10.5 h / 40 °C6: 94.4 percent / NaIO4 / methanol; H2O / 1 h / 0 °C  

With  3 A molecular sieve; pyridinium chlorochromate in  dichloromethane 24 h;  Ambient temperature;