Multi-step reaction with 11 steps
1.1: 98 percent / 2,6-lutidine / CH2Cl2 / 5 h / 20 °C
2.1: 95 percent / silver trifluoroacetate; I2; sodium bicarbonate / CHCl3 / 3 h / 0 °C
3.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C
4.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C
5.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C
6.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C
6.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C
6.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C
7.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C
8.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C
9.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C
10.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
11.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
With
2,6-dimethylpyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; borane-THF; oxalyl dichloride; di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; iodine; silver trifluoroacetate; sodium hydrogencarbonate; 1,1-diphenyl-L-valinol; dimethyl sulfoxide; diethylamine; triethylamine; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; dimethyl sulfoxide;
3.1: Sonogashira coupling / 5.1: Swern oxidation / 7.1: Swern oxidation;
DOI:10.1016/S0040-4020(00)00862-0