Multi-step reaction with 10 steps
1.1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C
2.1: 86 percent / sodium hydride / tetrahydrofuran / 0.5 h / 20 °C
3.1: 71 percent / H2 / palladium on carbon / CH2Cl2 / 10 h / 181 Torr
4.1: 85 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 30 h / 20 °C
5.1: 77 percent / pyridine / CH2Cl2 / 20 °C
6.1: 79 percent / H2SO4; acetic acid / 0.5 h / 20 °C
7.1: 88 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 3 h / 50 °C
8.1: NaOH; pyridine / 0.33 h / 20 °C
8.2: 82 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / 20 °C
9.1: 59 percent / H2 / palladium hydroxide on carbon / methanol
10.1: 100 percent / pyridine / 40 °C
With
pyridine; sodium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; hydrogen; L-Selectride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine;
palladium dihydroxide; palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane;
1.1: Swern oxidation / 2.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/S0968-0896(03)00115-9