Multi-step reaction with 4 steps
1: 1.) TBAF, 2.) IBX / 1.) THF, room temperature, 3 h, 2.) DMSO, room temperature, 14-20 h
2: 1.) NaClO2, NaH2PO4*H2O, 2.) NaHCO3, DDQ / 1.) t-BuOH, 2-methyl-2-butene, H2O, room temperature, 5 h, 2.) CH2Cl2, room temperature, 5 h
3: 33 percent / 2,2'-pyridyl disulfide, PPh3, AgClO4 / benzene / 18 h / Heating
4: 58 percent / Dowex-50 / methanol / 96 h / Ambient temperature
With
sodium chlorite; sodium dihydrogenphosphate; 2,2'-dipyridyldisulphide; Dowex-50; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydrogencarbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
methanol; benzene;
DOI:10.1021/jo961686+