Multi-step reaction with 12 steps
1: TFA / CHCl3 / 5 h / Ambient temperature
2: 97 percent / L-Selectride / tetrahydrofuran / 3 h / Ambient temperature
3: 88 percent / NaH, imidazole, Bu4NI / tetrahydrofuran; dimethylformamide / 11 h / 0 - 20 °C
4: NaBH3CN, AcOH / various solvent(s) / 48 h / Ambient temperature
5: DBU / benzene / 14 h / Ambient temperature
6: 95 percent / tetrahydrofuran / 16 h / Ambient temperature
7: tetrabutylammonium oxone / CH2Cl2 / 1.5 h / 0 °C
8: CaCO3 / xylene / 0.25 h / Heating
9: 96 percent / LiAlH4 / tetrahydrofuran / 8 h / Ambient temperature
10: OsO4 / Ambient temperature
11: 53 percent / K3Fe(CN)6, OsO4 / 2-methyl-propan-2-ol / 0.92 h
12: 1.) MeO2CN--SO2N+Et3, 3.) H2O
With
1H-imidazole; osmium(VIII) oxide; lithium aluminium tetrahydride; Burgess Reagent; Oxone tetrabutylammonium salt; water; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; sodium cyanoborohydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; calcium carbonate; potassium hexacyanoferrate(III);
In
tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; xylene; tert-butyl alcohol; benzene;
DOI:10.1021/ja973464e