Multi-step reaction with 9 steps
1: 75 percent / KOH / H2O; ethanol / 5 h / Heating
2: 85 percent / 4-(dimethylamino)pyridine; CuSO4; triflyl azide / CH2Cl2 / 2 h
3: NaOH; NBu4HSO4 / benzene; H2O / 1 h
4: 0.88 g / N-methylmorpholine oxide; OsO4 / H2O; acetone; tetrahydrofuran / 10 h
5: 85 percent / Na2CO3; Pb(OAc)4 / benzene / 3 h / 20 °C
6: 82 percent / triethylamine; NaBH(OAc)3 / 1,2-dichloro-ethane / 45 h
7: 85 percent / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tertramethyluronium*PF6; diisopropylethylamine / dimethylformamide / 15 h / 20 °C
8: 99 percent / formic acid / 20 h / 20 °C
9: N,N'-dicyclohexylcarbodiimide / ethyl acetate / 2 h / 0 °C
With
lead(IV) acetate; dmap; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; formic acid; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; sodium tris(acetoxy)borohydride; sodium carbonate; copper(II) sulfate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; HATU;
In
tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo0356863