Multi-step reaction with 13 steps
1.1: SOCl2 / dimethylformamide / 3 h / Heating
2.1: NaN3 / acetone; H2O / 0.25 h / 20 °C
3.1: 2-(trimethylsilyl)ethanol / xylene / 16 h / Heating
3.2: TBAF / tetrahydrofuran / 0.5 h / 20 °C
4.1: tetrahydrofuran / 1 h / 20 °C
5.1: BH3*DMS / tetrahydrofuran / 3 h / 2 °C
6.1: 99 percent / DMAP / tetrahydrofuran / 96 h / Heating
7.1: 89 percent / LiOH; H2O / methanol / 0.5 h / 50 °C
8.1: 92 percent / BH3*DMS / tetrahydrofuran / 3 h / 2 °C
9.1: benzene; tetrahydrofuran / 16 h / 20 °C
10.1: CS2CO3 / dimethylformamide / 16 h / 20 °C
11.1: 91 percent / NaOH; H2O / methanol / 1 h / 20 °C
12.1: dimethylformamide / 0.17 h / 50 °C
13.1: 66 percent / dimethylformamide / 2 h / 20 °C
With
dmap; lithium hydroxide; sodium hydroxide; thionyl chloride; sodium azide; 2-(Trimethylsilyl)ethanol; dimethylsulfide borane complex; water; caesium carbonate;
In
tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone; xylene; benzene;
1.1: Substitution / 2.1: Substitution / 3.1: Rearrangement / 3.2: Substitution / 4.1: Formylation / 5.1: Reduction / 6.1: Substitution / 7.1: Hydrolysis / 8.1: Reduction / 9.1: Substitution / 10.1: Acylation / 11.1: Hydrolysis / 12.1: Substitution / 13.1: Acylation;
DOI:10.1039/a904067f