Multi-step reaction with 12 steps
1: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
2: 97 percent / NBS, NaOAc / tetrahydrofuran; H2O / 0.5 h / 0 °C
3: CrO3 / acetic acid / 0.5 h / Ambient temperature
4: sodium triacetoxyborohydride / propan-2-ol / 0.5 h / -20 °C
5: 83 percent / iPr2EtN, DMAP / CH2Cl2 / 10 h / Ambient temperature
6: 88 percent / AcOH, H2O / tetrahydrofuran / 8 h / 40 °C
7: 99 percent / Et3N, DMAP / CH2Cl2 / 5 h / Ambient temperature
8: 99 percent / iPr2EtN, DMAP / CH2Cl2 / 10 h / Ambient temperature
9: 98 percent / AcOH, H2O / tetrahydrofuran / 5 h / 40 °C
10: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h
11: 19 percent / Et3N / 2 h / 0 °C
12: 99 percent / pyridine / 3 h / Ambient temperature
With
chromium(VI) oxide; dmap; N-Bromosuccinimide; oxalyl dichloride; water; sodium acetate; L-Selectride; sodium tris(acetoxy)borohydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; pyridine; dichloromethane; water; acetic acid; isopropyl alcohol;
DOI:10.1016/S0040-4020(99)00023-X