Multi-step reaction with 17 steps
1.1: sodium hydroxide / methanol; H2O / 3 h / 45 °C
2.1: 2.72 g / TMSCl / 13 h / 20 °C
3.1: 95 percent / imidazole / CH2Cl2 / 15 h / 20 °C
4.1: AlMe3 / CH2Cl2; toluene / 0.67 h / 0 °C
4.2: 68 percent / CH2Cl2; toluene / 22 h / 0 - 20 °C
5.1: DIBAL-H / toluene; hexane / 2 h / -78 °C
6.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 2 h / 20 °C
7.1: BuLi / tetrahydrofuran; hexane / 0.42 h / -10 °C
7.2: 161 mg / tetrahydrofuran; hexane / 0.5 h / -78 °C
8.1: 91 percent / molecular sieves 4 Angstroem; TBAF / tetrahydrofuran / 16 h / 20 °C
9.1: 81 percent / PTSA; Na2SO4 / CH2Cl2 / 4 h / 20 °C
10.1: 93 percent / NaH / dimethylformamide / 0 °C
11.1: 100 percent / PTSA / methanol / 24 h / 20 °C
12.1: 76 percent / N-bromosuccinimide / CH2Cl2 / 0.33 h / 0 °C
13.1: 100 percent / pyridine; 4-(dimethylamino)pyridine / 20 °C
14.1: 62 percent / NIS; trifluoromethanesulfonic acid / CH2Cl2 / 4 h / 20 °C
15.1: Me3P / tetrahydrofuran; toluene / 0.5 h / 20 °C
15.2: water / toluene; tetrahydrofuran / 0.67 h / Heating
16.1: CH2Cl2 / 1 h / 20 °C
17.1: methylamine / methanol; H2O / 72 h / 20 °C
With
pyridine; 1H-imidazole; dmap; sodium hydroxide; N-Bromosuccinimide; N-iodo-succinimide; n-butyllithium; chloro-trimethyl-silane; trifluorormethanesulfonic acid; 4 A molecular sieve; tetrabutyl ammonium fluoride; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; sodium sulfate; methylamine; trimethylphosphane;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo050727b