Multi-step reaction with 10 steps
1: 96 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / Ambient temperature
2: 40.9 percent / Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 0.25 h / Ambient temperature
3: 95 percent / Na2CO3 / tetrahydrofuran; H2O / 5 h / Heating
4: 1.) Zn-Ag couple, 2.) / 1.) ether, reflux, 2.) reflux, 4 h
5: PDC / dimethylformamide / 3 h / Ambient temperature
6: KOH, NH2OH*HCl / methanol / 3 h / Ambient temperature
7: 1.) diphenyl disulfide, n-Bu3P, 2.) sodium cyanoborohydride, acetic acid / 1.) THF, RT, 1 h, 2.) -70 deg C, 10 min
8: Et3N / CH2Cl2 / 3 h / Ambient temperature
9: 80percent aq. AcOH / 15 h / Heating
10: oxalyl chloride/DMSO / CH2Cl2 / 0.25 h / -60 °C
With
dmap; potassium hydroxide; dipyridinium dichromate; oxalyl dichloride; tributylphosphine; hydroxylamine hydrochloride; silver; sodium cyanoborohydride; sodium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diphenyldisulfane; zinc; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a038