Multi-step reaction with 9 steps
1: 75 percent / Me3NO, OsO4 / 2-methyl-propan-2-ol; pyridine; H2O / 12 h / Heating
2: 90 percent / DMAP / triethylamine / 3 h / Heating
3: 90 percent / TFA, H2O / CH2Cl2 / 24 h / Ambient temperature
4: 93 percent / pyridine / CH2Cl2 / 1 h / 0 °C
5: 60 percent / NaN3, benzo-15-crown-5 / dimethylformamide / Ambient temperature
6: 90 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C
7: 80 percent / tetrahydrofuran / 1 h / Ambient temperature
8: 91 percent / K2CO3 / methanol / 2 h / Ambient temperature
9: 80 percent / H2 / 20percent Pd(OH)2 on charcoal / ethanol
With
pyridine; dmap; osmium(VIII) oxide; sodium azide; 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; trimethylamine-N-oxide; water; hydrogen; potassium carbonate; trifluoroacetic acid;
palladium hydroxide - carbon;
In
tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; triethylamine; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo9607828