Multi-step reaction with 12 steps
1: 42 percent / m-CPBA / CH2Cl2 / 20 °C
2: 93 percent / Bu4NF*3H2O / tetrahydrofuran / 20 °C
3: 79 percent / toluene / 95 °C
4: 76 percent / NaH / dimethylformamide / 20 °C
5: 97 percent / pyridine; DMAP / 6 h / 20 °C
6: 31 percent / pig liver esterase; phosphate buffer / H2O / pH 7
7: 82 percent / KOH / ethanol / Heating
8: 98 percent / H2 / Pd/C / ethanol / 20 h / 20 °C / 7600 Torr
9: 65 percent / EDC / dimethylformamide / 20 °C
10: 52 mg / pyridine / dimethylsulfoxide / 20 h / 20 °C
11: imidazole / dimethylformamide / 20 °C
12: 92 percent / Bu4NF*3H2O / tetrahydrofuran / 20 °C
With
pyridine; 1H-imidazole; dmap; potassium hydroxide; phosphate buffer; pig liver esterase; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo034143q