Multi-step reaction with 12 steps
1: 85 percent / O3
2: 1.) -78 deg C, 2 h, 2.) 20 deg C, 1 h
3: 90 percent / n-Bu4NF, KF*2H2O
4: H2
5: 87 percent / DMSO, oxalyl chloride
6: 1.) n-BuLi, 2.) HMPT / 1.) THF, -78 to -50 deg C, 1 h, 2.) 0 deg C
7: aq. NaOH / ethanol
9: 1.) lithium hexamethylsilazide / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C, 8 h
10: 1.) LiN(SiMe3)2 / 1.) -78 deg C, 1 h, 2.) -78 deg C, 2 h
11: m-chloroperoxybenzoic acid, H2O2 / CHCl3; H2O / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min
12: 55 percent / CHCl3; toluene / 12 h / 100 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; sodium hydroxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; ozone; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane;
In
ethanol; chloroform; water; toluene;
DOI:10.1039/c39850000143