Multi-step reaction with 16 steps
1: 35 percent / aq. NaH2PO4, o-H3PO4 / 3 h / 100 °C
2: 100 percent / p-TsOH*H2O / benzene / 1 h / Heating
3: 91 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.25 h / Ambient temperature
4: 77 percent / t-BuOK / dimethylsulfoxide / 0.25 h / Ambient temperature
5: 1.) t-BuLi, 2.) HMPA / 1.) THF, pentane, 0 deg C, 1 h, 2.) THF, pentane, -78 deg C, 30 min
6: oxalic acid / CH2Cl2 / 2 h / Ambient temperature
7: (COCl)2, DMSO / CH2Cl2 / 0.5 h / -78 °C
8: ZnBr2 / CH2Cl2 / 23 h / Ambient temperature
9: camphorsulfonic acid (CSA) / benzene / 18 h / Ambient temperature
10: 79 percent / dimethylsulfoxide; tetrahydrofuran / 1.75 h / 0 - 20 °C
11: 217 mg / H2 / 10percent Pd/C / methanol / 0.75 h / Ambient temperature
12: NaIO4, RuO2 / H2O; CCl4; acetonitrile / 1.5 h / 0 - 20 °C
13: diethyl ether / 0 °C
15: 82 percent / NaBH4 / methanol; tetrahydrofuran / 0.5 h / -20 °C
16: 4-(N,N-dimethylamino)pyridine (DMAP), unsym-N,N-dimethylethylenediamine / pyridine / 14.25 h / Ambient temperature
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; oxalyl dichloride; phosphoric acid; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; tert.-butyl lithium; pyridinium hydrobromide perbromide; oxalic acid; toluene-4-sulfonic acid; dimethyl sulfoxide; N,N-dimethylethylenediamine; zinc dibromide;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetonitrile; benzene;