Multi-step reaction with 15 steps
1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
2: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C
3: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C
4: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
5: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
6: 94 percent / K2CO3; MeOH / 2 h / 23 °C
7: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
8: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
9: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
10: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
11: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
12: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
13: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
14: 96 percent / K2CO3; MeOH / 1 h / 20 °C
15: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
With
pyridine; 1H-imidazole; methanol; dmap; 1,2,3-Benzotriazole; potassium phosphate; lithium borohydride; sulfurous dibromide; tetrakis(triphenylphosphine) palladium(0); hydrogen fluoride; potassium carbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; zinc(II) chloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
2: Suzuki-Miyaura cross-coupling reaction / 7: Dess-Martin oxidation / 8: Strecker reaction / 12: Dess-Martin oxidation / 13: Pomerantz-Frisch-type cyclization;
DOI:10.1021/ja0571794