Multi-step reaction with 14 steps
1.1: 71 percent / Et3N; N-methyl-2-chloropyridinium iodide / CH2Cl2 / 2.5 h / Heating
2.1: titanium tetra-isopropoxide / CH2Cl2 / 1 h / 40 °C
2.2: 97 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH2Cl2 / 3 h / Heating
3.1: CuCN / diethyl ether / -78 - 0 °C
3.2: 86 percent / diethyl ether / 1 h / -78 - -25 °C
4.1: 83 percent / LiAlH4 / diethyl ether / 0.67 h / 0 °C
5.1: 86 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C
6.1: diisopropylethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C
6.2: 94 percent / N,N-dimethyl-4-aminopyridine / toluene / 3 h / 20 °C
7.1: 88 percent / tetra-N-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C
8.1: 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C
9.1: dicyclohexylboron chloride; Me2NEt / diethyl ether / 1.5 h / 0 °C
9.2: diethyl ether / 19 h / -78 - -20 °C
9.3: aq. H2O2 / methanol / 3 h / 20 °C
10.1: 196 mg / 2,6-lutidine / CH2Cl2 / 2 h / -50 °C
11.1: K2CO3 / methanol / 2 h / 20 °C
12.1: 39.3 mg / aq. NaIO4 / 2-methyl-propan-2-ol / 12 h / 20 °C
13.1: 75.5 mg / Et3N; diphenylphosphoryl azide / dimethylformamide / 2 h / 20 °C
14.1: 93 percent / 2,6-dichloro-3,5-dicyanoquinone / CH2Cl2; aq. phosphate buffer / 1.5 h / 0 - 20 °C / pH 7
With
1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; sodium periodate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; N,N-dimethyl-ethanamine; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; diphenylphosphoranyl azide; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; 2,6-dichloro-3,5-dicyano-1,4-benzoquinone; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja036050w