Multi-step reaction with 8 steps
1: 96 percent / NaHCO3, m-chloroperbenzoic acid / CH2Cl2 / 14 h / Ambient temperature
2: 49 percent / CuI / tetrahydrofuran; diethyl ether / 14 h / -25 °C
3: 1.) camphorsulfonic acid, 2.) acetone / 1.) CH2Cl2, RT, 45 min, 2.) CH2Cl2, RT, 14 h
4: 96 percent / periodic acid, ruthenium trichloride hydrate / CCl4; acetonitrile; H2O / 2 h
5: 100 percent / diisopropylethylamine, diethylphosphoryl cyanide / CH2Cl2 / 14 h / Ambient temperature
6: 70 percent / acetyl chloride, ethanedithiol / methanol / 5 h
7: 90 percent / diisopropylethylamine, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / CH2Cl2 / 14 h
8: 40 percent / trifluoroacetic acid / CH2Cl2 / 0.25 h
With
ethandithiol; ruthenium trichloride; copper(l) iodide; diethylphosphoryl cyanide; camphor-10-sulfonic acid; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; periodic acid; N-ethyl-N,N-diisopropylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; acetone; trifluoroacetic acid;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/jm00112a005