Multi-step reaction with 16 steps
1.1: 95 percent / silver trifluoroacetate; I2; sodium bicarbonate / CHCl3 / 3 h / 0 °C
2.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C
3.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C
4.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C
5.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C
5.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C
5.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C
6.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C
7.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C
8.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C
9.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
10.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
11.1: 60 percent / various solvent(s) / 66 h / Heating
12.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
13.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
14.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
15.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
16.1: HCl / diethyl ether / 1 h / 20 °C
16.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
With
hydrogenchloride; dmap; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; copper(l) iodide; borane-THF; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 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;
2.1: Sonogashira coupling / 4.1: Swern oxidation / 6.1: Swern oxidation / 11.1: intramolecular Diels-Alder reaction;
DOI:10.1016/S0040-4020(00)00862-0