Multi-step reaction with 12 steps
1.1: 79.3 percent / BF3*Et2O / CH2Cl2 / 0.5 h / 0 °C
2.1: 81 percent / dimethylsulfoxide / 12 h / 75 °C
3.1: DIBAL / toluene; CH2Cl2 / 1 h / -78 °C
4.1: 181 mg / NaBH4 / methanol / 0.5 h / 0 °C
5.1: 92 percent / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
6.1: HIO4 / ethyl acetate / 6 h / 0 °C
7.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
8.1: 49 mg / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
9.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
9.2: 78 percent / tetrahydrofuran / -78 - 20 °C
10.1: LiNEt2 / tetrahydrofuran; hexane / 0.17 h / -78 °C
10.2: 61 percent / tetrahydrofuran; hexane / 0.67 h / -78 °C
11.1: 81 percent / PPTS / 12 h / 30 °C
12.1: 93 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 2 h / 20 °C
With
pyridine; dmap; sodium tetrahydroborate; boron trifluoride diethyl etherate; lithium diethylamide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; periodic acid; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene;
8.1: Dess-Martin oxidation / 12.1: Dess-Martin oxidation;
DOI:10.1002/chem.200500892