Multi-step reaction with 21 steps
1: 99 percent / NaH / paraffin; tetrahydrofuran / 1.) -78 deg C -> room temperature, 4 h, 2.) room temperature, 2 h
2: 21.2 g / Zn, AcOH / tetrahydrofuran; H2O / 1 h / Ambient temperature
3: Et3N / dimethylformamide / 4 h / Ambient temperature
4: 92 percent / Et3N / CH2Cl2 / 3 h / Ambient temperature
5: 94 percent / NaH, imidazole / paraffin; tetrahydrofuran / Heating
6: 98 percent / (HF)n*Py / 0.67 h / -10 °C
7: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / Ambient temperature
8: 1.) LiN(TMS)2, 2.) NaBH4 / 1.) THF, -78 deg C -> -5 deg C, 3 h, 2.) H2O, 0 deg C, 20 min
9: 80 percent / Et3N, DMAP / CH2Cl2 / Ambient temperature
10: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / Ambient temperature
11: 94 percent / (HF)n*Py / Ambient temperature
12: 63 percent / DBU / tetrahydrofuran / Ambient temperature
13: 88 percent / NaBH4 / tetrahydrofuran; H2O / 1 h / Ambient temperature
14: 75 percent / Et3N, DMAP / CH2Cl2 / 7 h / Ambient temperature
15: 85 percent / Ph3P, Pd(PPh3, octanoic acid / tetrahydrofuran / Ambient temperature
16: 66 percent / MCPBA / CH2Cl2 / 0 °C
17: 66 percent / NaHCO3 / 5 h / -5 - 10 °C
18: 90 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / Ambient temperature
19: 85 percent / (HF)n*Py / 1.) -10 deg C -> room temperature, 2.) room temperature, 2 h
20: 88 percent / K2CO3 / methanol / 0 - 20 °C
21: 88 percent / pyridine / 0 - 20 °C
With
1H-imidazole; dmap; sodium tetrahydroborate; Octanoic acid; (HF)n*Py; Pd(PPh3; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; zinc;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; paraffin;
DOI:10.1016/S0040-4020(97)00652-2