Multi-step reaction with 16 steps
1.1: 84 percent / (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -35 °C
2.1: 90 percent / 4-(dimethylamino)pyridine / acetonitrile / 5 h
3.1: 85 percent / IBr / toluene; CH2Cl2 / 1 h / -85 °C
4.1: 96 percent / K2CO3; methanol / 2 h / 20 °C
5.1: 92 percent / PPh3; DEAD / tetrahydrofuran / 2 h / 20 °C
6.1: 77 percent / K2CO3; methanol / H2O / 2 h / 20 °C
7.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 3 h / 20 °C
8.1: CuI / diethyl ether / 0.25 h / -30 °C
8.2: 92 percent / diethyl ether / 0.5 h / -40 °C
9.1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C
10.1: 88 percent / dimethylformamide; H2O / 20 h / 50 °C
11.1: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C
12.1: tetrahydrofuran / 0 - 20 °C
13.1: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C
14.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C
15.1: 82 percent / tetrahydrofuran / 13 h / 65 °C
With
methanol; dmap; sodium hydroxide; copper(l) iodide; (+)-β-chlorodiisopinocampheylborane; dihydrogen peroxide; iodine(I) bromide; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo020501y