Multi-step reaction with 12 steps
1.1: 91 percent / CeCl3*7H2O; oxalic acid / acetonitrile / 2 h / 20 °C
2.1: oxalyl chloride; dimethylsulfoxide; triethylamine / CH2Cl2 / -60 - 20 °C
3.1: 74 percent / CH3MgCl / tetrahydrofuran; CH2Cl2 / 20 °C
4.1: 88 percent / DIPEA / CHCl3 / 6 h / 20 - 60 °C
5.1: 2,6-lutidine; tert-butyldimethylsilyl triflate / CH2Cl2 / 3 h / 20 °C
5.2: 86 percent / KF monohydrate / methanol / 40 h / 20 °C
6.1: 94 percent / potassium carbonate / methanol / 1 h / 20 °C
7.1: 90 percent / acetic acid / CH2Cl2 / 2 h / 20 °C
8.1: oxalyl chloride; dimethylsulfoxide; triethylamine / CH2Cl2 / -60 - 20 °C
9.1: 378 mg / zinc(II) chloride / CH2Cl2; tetrahydrofuran / 0.67 h / 23 °C
10.1: 90 percent / acetic acid; zinc / diethyl ether / 1.5 h / 23 °C
11.1: 94 percent / potassium carbonate / acetonitrile / 4 h / 20 °C
12.1: 93 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
With
2,6-dimethylpyridine; dmap; cerium(III) chloride; oxalyl dichloride; t-butyldimethylsiyl triflate; methylmagnesium chloride; oxalic acid; potassium carbonate; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; zinc;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; acetonitrile;
2.1: Swern oxidation / 7.1: Pictet-Spengler reaction / 8.1: Swern oxidation / 9.1: Strecker reaction;
DOI:10.1002/anie.200603179