Multi-step reaction with 11 steps
1.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 1 h
2.1: NaHMDS / tetrahydrofuran / -78 - 20 °C
2.2: 75 percent / tetrahydrofuran / -78 - 20 °C
3.1: aq. KOH / ethanol; tetrahydrofuran / 6 h / Heating
4.1: Et3N / tetrahydrofuran / 0.25 h / -10 °C
4.2: 1.79 g / NaBH4 / tetrahydrofuran; H2O / 0 °C
5.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating
6.1: 74 percent / diisobutylaluminum hydride / hexane; CH2Cl2 / -78 - 0 °C
7.1: Dess-Martin periodinane / CH2Cl2 / 1 h
8.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / -78 °C
8.2: 2.01 g / tetrahydrofuran / 3 h / -78 - 0 °C
9.1: 97 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0 °C
10.1: aq. KOH / ethanol; tetrahydrofuran / 6 h / Heating
11.1: Et3N / tetrahydrofuran / -78 - 0 °C
11.2: 1.52 g / LiCl / tetrahydrofuran / 0 - 20 °C
With
pyridine; dmap; potassium hydroxide; sodium tetrahydroborate; potassium tert-butylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; nickel dichloride;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane;
1.1: Dess-Martin oxidation / 2.2: Wittig coupling / 7.1: Dess-Martin oxidation / 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033