Multi-step reaction with 11 steps
1: conc. H2SO4 / 2 h / Ambient temperature
2: 80 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature
3: NaI, NaHCO3 / acetone / 72 h / Ambient temperature
4: 1.) LDA, 2.) HMPA / 1.) THF, -78 deg C, 1 h, 2.) 5 min
5: 98 percent / Na2HPO4, 6percent sodium amalgam / methanol / 1 h / -20 °C
6: 1.) LDA / 1.) THF, -30 deg C, 0.5 h, 2.) -78 deg C
7: DIBAL / hexane; tetrahydrofuran / 1 h / -78 °C
8: 53 percent / Raney Ni / ethanol / 0.5 h
9: 74 percent / 10 N KOH / ethane-1,2-diol / 4 h / 165 °C
10: 1.) di-(2-pyridyl) disulfide, Ph3P, 2.) AgClO4 / 1.) benzene, 1 h, 2.) CH3CN, 160 deg C, 30 min
11: 17 percent / BBr3 / CH2Cl2 / 0.5 h / 0 - 20 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; 2,2'-dipyridyldisulphide; sulfuric acid; silver perchlorate; boron tribromide; nickel; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; sodium iodide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethylene glycol; acetone;
DOI:10.1016/0957-4166(90)90013-Z