Multi-step reaction with 15 steps
1: 88 percent / m-CPBA / CH2Cl2 / 0.5 h / 25 °C
2: 80 percent / 14 h / 25 °C
3: 98 percent / K2CO3 / methanol / 2 h / 25 °C
4: 98 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 25 °C
5: 89 percent / H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr
6: 1.) NaH, 2.) n-Bu4NI / 1.) THF, 10 min, 2.) THF, 25 deg C, 1 h
7: 98 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C
8: 1.) Pd(PPh3)4, n-PrNH2, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 5 h
9: m-CPBA / CH2Cl2 / 1 h / 25 °C
10: 82 percent / 48percent aq. HBr / tetrahydrofuran / 2 h / 25 °C
11: 1.) AgNO3, 2.) KCN / 1.) THF, EtOH, H2O, 25 deg C, 1 h, 2.) THF, EtOH, H2O, 25 deg C, 10 min
12: 59 percent / sat. aq. NaHCO3, m-CPBA / CH2Cl2 / 1 h / 25 °C
13: 42 percent / LDA / toluene; cyclohexane / 0.33 h / -78 °C
14: D2O / Irradiation
15: aq. potassium phosphate monobasic-sodium hydroxide buffer / tetrahydrofuran / 1.5 h / 25 °C / pH 8.0
With
2,6-dimethylpyridine; propylamine; potassium cyanide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium phosphate monobasic-sodium hydroxide buffer; hydrogen bromide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; silver nitrate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; water-d2; toluene;
DOI:10.1021/ja00049a023