Multi-step reaction with 11 steps
1: LiAlH4 / diethyl ether / 1 h / Ambient temperature
2: PBr3 / diethyl ether / 1 h
3: 58 percent / ethanol / 1 h / Heating
4: aq. NaIO4 / methanol / 6 h / Ambient temperature
5: KMnO4 / methanol; H2O / 0.5 h / Ambient temperature
6: 84 percent / NBS, azobis(isobutyronitrile) / CCl4 / 2 h / Heating; Irradiation
7: ethanol / 1 h / Ambient temperature
8: 80 percent / LDA, TMEDA / tetrahydrofuran / 1 h / -78 °C
9: 1.) OsO4, NaIO4, 2.) 1,5-diazabicyclo<5.4.2>undecene (DBU) / 1.) THF/H2O/ether, RT, 1 h, 2.) THF, overnight
10: 20 percent / H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature
11: triethylamine / CH2Cl2 / 1 h / 0 °C
With
potassium permanganate; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; hydrogen; phosphorus tribromide; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water;
DOI:10.1021/jo00323a016