Multi-step reaction with 7 steps
1.1: Na / diethyl ether; liquid ammonia / 0.83 h / -78 - 22 °C
1.2: 98 percent / ammonium chloride / diethyl ether / 12 h / 22 °C
2.1: 98 percent / DMSO; (COCl)2; ET3N / CH2Cl2 / 2.33 h / -78 - 22 °C
3.1: triphenylphosphine; zinc / CH2Cl2 / 22 °C
3.2: 63 percent / triphenylphosphine; zinc / CH2Cl2 / 22 °C
4.1: 88 percent / HF / acetonitrile; H2O / 0.67 h / 0 °C
5.1: sodium hydride / tetrahydrofuran; various solvent(s) / 1.5 h / 0 °C
5.2: 94 percent / sodium iodide / tetrahydrofuran; various solvent(s) / 22.5 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
6.2: 80 percent / sodium iodide / tetrahydrofuran / 3 h / 0 °C
7.1: diisopropylethylamine / CH2Cl2 / 0 °C
With
n-butyllithium; oxalyl dichloride; hydrogen fluoride; sodium; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; ammonia; water; acetonitrile;
2.1: Swern oxidation;
DOI:10.1021/ol0201557