Multi-step reaction with 11 steps
1: 84 percent / PCl3 / CHCl3 / 40 h / Ambient temperature
2: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C
3: 83 percent / methanol / Ambient temperature
4: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.83 h / Ambient temperature
5: 99 percent / Na/Hg, NaH2PO4 / methanol / 1 h
6: 1.) n-BuLi / 1.) THF, -78 to -50 deg C, 40 min, 2.) THF, -50 deg C, 5 min, then room temp., 30 min
8: 96 percent / ammonium molybdate, aq. H2O2 / ethanol / 17 h
9: 94 percent / aq. HCl / tetrahydrofuran / 8 h / Ambient temperature
10: 1.) LiCl, MsCl, 2,6-lutidine, 2.) NaHMDS / 1.) DMF, room temp., 2 h, 2.) THF, reflux, 2.5 h
11: 97 percent / p-TsNHNH2, NaOAc / tetrahydrofuran; H2O / 14.5 h / Heating
With
2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; sodium dihydrogenphosphate; sodium amalgam; n-butyllithium; ammonium molybdate; dihydrogen peroxide; sodium acetate; sodium hexamethyldisilazane; methanesulfonyl chloride; toluene-4-sulfonic acid hydrazide; lithium chloride; phosphorus trichloride;
In
tetrahydrofuran; methanol; ethanol; hexane; chloroform; water; dimethyl sulfoxide;
DOI:10.1021/jo9801770