Multi-step reaction with 12 steps
1.1: 83 percent / NaH / tetrahydrofuran / 6 h / 20 °C
2.1: 85 percent / CSA / methanol; H2O / 12 h / 20 °C
3.1: 66 percent / Et3N / CH2Cl2 / 16 h / 20 °C
4.1: 88 percent / K2CO3 / methanol / 1 h / 20 °C
5.1: 93 percent / n-BuLi / toluene / 12 h / -20 - 20 °C
6.1: 92 percent / imidazole / CH2Cl2 / 4 h / 20 °C
7.1: 56 percent / BH3*Me2S; aq. NaOH; H2O2 / tetrahydrofuran; methanol / 12 h / 20 °C
8.1: 98 percent / IBX / dimethylsulfoxide / 6 h / 20 °C
9.1: TiCl4; TMEDA / CH2Cl2 / 0.5 h / 0 °C
9.2: 54 percent / CH2Cl2 / 0.5 h / -78 °C
10.1: 80 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 20 °C
11.1: 83 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C
12.1: 92 percent / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 3 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; N,N,N,N,-tetramethylethylenediamine; dimethylsulfide borane complex; camphor-10-sulfonic acid; dihydrogen peroxide; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;
DOI:10.1016/j.tetasy.2004.06.023