Multi-step reaction with 13 steps
1.1: 90 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.08 h
2.1: 94 percent / sulfur trioxide pyridine complex; DIPEA; dimethyl sulfoxide / CH2Cl2 / 0.25 h / 0 °C
3.1: MgBr2*OEt2 / CH2Cl2 / 20 °C
3.2: 73 percent / hydrazine acetate / CH2Cl2; methanol / 12 h / 20 °C
4.1: acetyl chloride / toluene / 0 - 20 °C
4.2: 70 percent / water / toluene / 0 - 20 °C
5.1: 4-dimethylaminopyridine; N,N'-diisopropylcarbodiimide / CH2Cl2 / 2.5 h / 0 °C
6.1: bis(trifluoroacetoxy)iodobenzene; water; NaHCO3 / acetonitrile / 0.5 h / 20 °C
6.2: trifluoroacetic acid / H2O / 0.5 h / 50 °C
7.1: 461 mg / DBU / CH2Cl2 / 0.5 h / 0 - 20 °C
8.1: TMSOTf / CH2Cl2 / 0.5 h / -20 - -10 °C
9.1: 96 percent / pyridine; acetic acid; hydrazine monohydrate / CH2Cl2 / 1.5 h / 20 °C
10.1: 81 percent / TMSOTf / CH2Cl2 / 0.5 h / -25 °C
11.1: H2O2; LiOH; H2O / tetrahydrofuran / 16 h / 20 °C
11.2: 85 percent / aq. KOH; MeOH / tetrahydrofuran / 16 h / 20 °C
12.1: 82 percent / SO3*Et3N / pyridine / 4 h / 20 °C
13.1: 87 percent / aq. NaOH; PMe3 / tetrahydrofuran / 4 h
With
pyridine; triethylsilane; dmap; lithium hydroxide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; water; dihydrogen peroxide; triethylamine sulfurtrioxide; sulfur trioxide pyridine complex; sodium hydrogencarbonate; hydrazine hydrate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; magnesium bromide; diisopropyl-carbodiimide; trimethylphosphane;
trimethylsilyl trifluoromethanesulfonate;
In
tetrahydrofuran; pyridine; dichloromethane; toluene; acetonitrile;
2.1: Parikh-Doering oxidation / 4.1: Pinner reaction / 13.1: Staudinger reaction;
DOI:10.1002/chem.200700141