Multi-step reaction with 16 steps
1.1: TMSOTf
2.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: tetrahydrofuran; hexane / 1 h / -78 °C
3.1: tetrahydrofuran; hexane / 1 h / 20 °C
4.1: t-BuOK / tetrahydrofuran; hexane / 3 h / 30 °C
5.1: 97 percent / p-TsOH; H2O / acetone; tetrahydrofuran / 14 h / 40 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
6.2: tetrahydrofuran; hexane
7.1: tetrahydrofuran; hexane / 1 h / 20 °C
8.1: t-BuOK / tetrahydrofuran; hexane / 3 h / 20 °C
9.1: p-TsOH; H2O / tetrahydrofuran; acetone / 14 h / 40 °C
10.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
10.2: tetrahydrofuran; hexane
11.1: tetrahydrofuran; hexane / 1 h / 20 °C
12.1: t-BuOK / tetrahydrofuran; hexane / 3 h / 20 °C
13.1: p-TsOH; H2O / tetrahydrofuran; acetone / 14 h / 40 °C
14.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
14.2: tetrahydrofuran; hexane
15.1: tetrahydrofuran; hexane / 1 h / 20 °C
16.1: t-BuOK / tetrahydrofuran; hexane / 3 h / 20 °C
With
n-butyllithium; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; water; toluene-4-sulfonic acid;
In
tetrahydrofuran; hexane; acetone;
1.1: Etherification / 2.1: Metallation / 2.2: Addition / 3.1: Substitution / 4.1: Elimination / 5.1: Hydrolysis / 6.1: Metallation / 6.2: Addition / 7.1: Substitution / 8.1: Elimination / 9.1: Hydrolysis / 10.1: Metallation / 10.2: Addition / 11.1: Substitution / 12.1: Elimination / 13.1: Hydrolysis / 14.1: Metallation / 14.2: Addition / 15.1: Substitution / 16.1: Elimination;