Multi-step reaction with 16 steps
1.1: 92 percent / EDC*H2O; HOBt*H2O; Et3N / CH2Cl2 / 12 h / 25 °C
2.1: 80 percent / Burgess reagent / tetrahydrofuran / 4 h / Heating
3.1: 90 percent / DBU; BrCCl3 / CH2Cl2 / 3 h / 25 °C
4.1: 83 percent / LiBH4 / ethanol; tetrahydrofuran / 0 - 25 °C
5.1: NaHMDS / tetrahydrofuran / -78 °C
5.2: 72 percent / n-tetrabutylammonium iodide / tetrahydrofuran / 36 h / 25 °C
6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
6.2: 73 percent / tetrahydrofuran; hexane / 0.08 h / -78 °C
7.1: 47 percent / p-toluenesulfonic acid monohydrate / 1,2-dichloro-ethane / 0.42 h / Heating
8.1: 4.6 g / aq. NaHCO3 / dioxane / 2 h / 25 °C
9.1: 85 percent / K2CO3 / acetone / 0 - 25 °C
10.1: aq. LiOH / tetrahydrofuran; methanol / 0.33 h / Heating
11.1: trifluoroacetic acid / 0.17 h
12.1: 0.220 g / HATU; 2,4,6-collidine / CH2Cl2; dimethylformamide / 12 h / 25 °C
13.1: 65 percent / BCl3 / CH2Cl2 / 2 h / -78 °C
14.1: 70 percent / Et3N; 4-dimethylaminopyridine / dioxane / 1 h / 25 °C
15.1: 1-hydroxy-1,2-benziodoxol-3(1H)-one / dimethylsulfoxide / 2 h / 25 °C
16.1: 0.072 g / NaClO2; resorcinol; aq. NaH2PO4 / dimethylsulfoxide / 2 h / 25 °C
With
2,4,6-trimethyl-pyridine; dmap; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium borohydride; n-butyllithium; 1-hydroxy-1,2-benzodioxol-3-(1H)-one; Burgess Reagent; Bromotrichloromethane; sodium hexamethyldisilazane; boron trichloride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; recorcinol;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja040092i