Multi-step reaction with 17 steps
1: 100 percent / imidazole / CH2Cl2 / 1 h / 0 °C
2: 93 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 1 h / 20 °C
3: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / 20 °C
4: 96 percent / triethylamine; sulfur trioxide pyridine complex / dimethylsulfoxide; CH2Cl2 / 3 h / 20 °C
5: 99 percent / MgBr2*Et2O / CH2Cl2 / 3 h / 20 °C
6: osmium tetroxide; NMO / acetone; H2O / 1.5 h / 20 °C
7: NaIO4 / acetone; H2O / 0.5 h / 20 °C
8: 3.24 g / NaBH4 / ethanol / 0.5 h / 20 °C
9: 93 percent / pyridine; DMAP / CH2Cl2 / 24 h / 20 °C
10: 88 percent / CAN / acetonitrile; H2O / 0.5 h / 20 °C
11: 99 percent / triethylamine / CH2Cl2 / 3 h / 0 °C
12: 99 percent / aq. HCl / acetonitrile / 2 h / 20 °C
13: 68 percent / p-TsOH*H2O / CHCl3 / 12 h / Heating
14: 99 percent / NaI / acetone / 2 h / Heating
15: Bu3SnH; Et3B / toluene; hexane / 1 h / -78 °C
16: 312 mg / K2CO3 / methanol / 2 h / 20 °C
17: 98 percent / triethylamine / CH2Cl2 / 2.5 h / 0 °C
With
pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; triethyl borane; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; potassium carbonate; toluene-4-sulfonic acid; triethylamine; sodium iodide; magnesium bromide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/ja0279646