Multi-step reaction with 13 steps
1.1: 88 percent / imidazole / dimethylformamide / 1.5 h / 0 °C
2.1: 96 percent / pyridine / CH2Cl2 / 1 h / 0 °C
3.1: Pd2dba3*CHCl3; (S)-BINAPO / dimethylformamide / 21 h / 0 °C
4.1: 100 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C
5.1: 90 percent / PBr3 / tetrahydrofuran / 1.5 h / 0 - 20 °C
6.1: 95 percent / dimethylsulfoxide / 1 h / 20 °C
7.1: 73 percent / Pd(OAc)2; Me2PPh; Ag2CO3 / dimethylsulfoxide / 17 h / 90 °C
8.1: LiAlH4 / tetrahydrofuran / 1.5 h / 20 °C
9.1: 3.22 g / Et3N / dimethylformamide / 1 h / 20 °C
10.1: 77 percent / MnO2; benzoquinone; AcOH / Pd(OAc)2 / 20 h / 50 °C
11.1: 9-BBN / tetrahydrofuran / 9 h / 50 °C
11.2: aq. NaOH; H2O2 / tetrahydrofuran / 4 h / 20 °C
12.1: 87 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C
13.1: 63 percent / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C
With
pyridine; 1H-imidazole; hydrogenchloride; manganese(IV) oxide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; palladium diacetate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; phosphorus tribromide; potassium hexamethylsilazane; acetic acid; dimethyl sulfoxide; triethylamine; silver carbonate; (S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide); Dimethyl(phenyl)phosphine; p-benzoquinone;
palladium diacetate;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
7.1: Heck reaction / 12.1: Swern oxidation;
DOI:10.1021/ja029382u