Multi-step reaction with 16 steps
1.1: HCO2H; triethylamine / Noyori (R,R)-catalyst / dimethylformamide / 24 h / 0 - 40 °C
1.2: diphenylphosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene; dimethylformamide / 24 h / 50 °C
1.3: H2 / Pd/C / ethyl acetate / 15 h / 25 °C
2.1: acetic acid; NaCNBH3; MgSO4 / methanol / 4 h / 0 - 65 °C
3.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C
4.1: 84 percent / NaH / dimethylformamide / 2 h / 0 - 25 °C
5.1: 90 percent / HCl / dioxane / 72 h / 0 - 25 °C
6.1: 85 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; triethylamine / CH2Cl2 / 24 h / 0 - 25 °C
7.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; buffer solution / CH2Cl2 / 0.5 h / 25 °C / pH 7
8.1: 61 percent / Cu(OTf)2 / benzene / 0.25 h / 85 °C
9.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 5 h / 25 °C
10.1: 93 percent / tributyltin hydride; acetic acid / [(PPh3)2PdCl2] / 1 h / 0 - 25 °C
11.1: CHF2COOH; MgSO4 / benzene / 0.75 h / 100 °C
12.1: 100 percent / triethylamine / CH2Cl2 / 0.5 h / 0 °C
13.1: 92 percent / tetrabutylammonium iodide / toluene / 3 h / 110 °C
14.1: tetrabutylammonium fluoride / CH2Cl2 / 0.03 h / 0 °C
15.1: N,N-diisopropylethylamine / CH2Cl2 / 0.5 h
16.1: 2,2-dimethyldioxirane / CH2Cl2 / 1.5 h / 0 - 25 °C
With
hydrogenchloride; Difluoroacetic acid; formic acid; 2,2-dimethyldioxirane; buffer solution; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; tetra-(n-butyl)ammonium iodide; copper(II) bis(trifluoromethanesulfonate); sodium hydride; sodium cyanoborohydride; magnesium sulfate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
bis-triphenylphosphine-palladium(II) chloride; ((1R,2R)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)ruthenium chloride(I) (4-cymene);
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1002/anie.200503983