Multi-step reaction with 12 steps
1: 97 percent / NBS, NaOAc / tetrahydrofuran; H2O / 0.5 h / 0 °C
2: CrO3 / acetic acid / 0.5 h / Ambient temperature
3: sodium triacetoxyborohydride / propan-2-ol / 0.5 h / -20 °C
4: 99 percent / DMAP, Py / CH2Cl2 / 3 h / Ambient temperature
5: 92 percent / Zn, CuSO4*5H2O, NaOAc / aq. acetic acid; tetrahydrofuran / 1 h / Ambient temperature
6: 99 percent / DBU / tetrahydrofuran / 1.5 h / Ambient temperature
7: 99 percent / aq. AcOH / 2 h / 40 °C
8: 99 percent / Et3N, DMAP / CH2Cl2 / 5 h / Ambient temperature
9: 99 percent / iPr2EtN, DMAP / CH2Cl2 / 1.5 h / Ambient temperature
10: 89 percent / AcOH, H2O / tetrahydrofuran / 5 h / 40 °C
11: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -65 °C
12: 94 percent / Et3N / diethyl ether / 1 h / 0 °C
With
pyridine; chromium(VI) oxide; dmap; N-Bromosuccinimide; oxalyl dichloride; water; sodium acetate; sodium tris(acetoxy)borohydride; copper(II) sulfate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; zinc;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; isopropyl alcohol;
DOI:10.1016/S0040-4020(99)00023-X