Multi-step reaction with 6 steps
1: 71 percent / SOBr2, 1,5-hexadiene / CH2Cl2 / 1 h / 0 °C
2: 1.) LDA, 2.) dimethylpropyleneurea (DMPU) / 1.) THF, hexane, -78 deg C, 2 h, 2.) from -78 deg C to RT, 21 h
3: 93 percent / 30percent H2O2, LiOH / tetrahydrofuran; H2O / 55 h / Ambient temperature
4: oxalyl chloride, DMF / toluene / 1.5 h / Heating
5: pyridine / CH2Cl2 / 0.5 h / 0 °C
6: iodine, AcOH / tetrahydrofuran; H2O / 48 h / 0 °C
With
pyridine; 1,3,4-trimethylimidazolidin-2-one; lithium hydroxide; sulfurous dibromide; oxalyl dichloride; 1,5-Hexadien; dihydrogen peroxide; iodine; acetic acid; N,N-dimethyl-formamide; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1021/jo00266a034