Multi-step reaction with 8 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: 1.) triethylamine, methanesulfonyl chloride, 2.) LiBr / 1.) CH2Cl2, 0 deg C, 30 min, 2.) acetone, reflux
3: 48 percent / dimethylformamide / Ambient temperature
4: 1.) n-BuLi / 1.) THF, -78 deg C, 45 min, 2.) a) THF, -78 deg C, 50 min, b) 0 deg C, 30 min
5: oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -78 °C
6: 74 mg / disodium hydrogen phosphate, Na/Hg / methanol / 2.5 h / 0 °C
7: 1.) O3, NaHCO3, 2.) dimethyl sulfide / 1.) MeOH, CH2Cl2, -78 deg C, 2.) a) -78 deg C, 10 min, b) RT, 1.5 h
8: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 5 min
With
disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide; sodium hydrogencarbonate; ozone; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium bromide; lithium diisopropyl amide;
In
methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00275a019