Multi-step reaction with 10 steps
1.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere
1.2: 0 °C / pH 7 / Inert atmosphere
2.1: pyridinium p-toluenesulfonate / 0.25 h / 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C / Inert atmosphere
3.2: -60 - 20 °C / Inert atmosphere
4.1: n-butyllithium / hexane; toluene / 0 - 20 °C / Inert atmosphere
4.2: -78 - 20 °C / Inert atmosphere
5.1: hydrogenchloride / water; acetic acid / 2.5 h / 80 °C
6.1: Hoveyda-Grubbs catalyst second generation / toluene / 1 h / 60 °C / Inert atmosphere
7.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethyl acetate / 2 h / 20 °C / Inert atmosphere
8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran
9.1: boron trifluoride diethyl etherate / dichloromethane / Inert atmosphere
10.1: pyridine / 3 h / 20 °C
With
hydrogenchloride; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; pyridine; hexane; dichloromethane; water; acetic acid; ethyl acetate; toluene;
3.1: Swern oxidation / 3.2: Swern oxidation / 4.2: Wittig reaction / 8.1: Mitsunobu reaction;
DOI:10.1016/j.carres.2011.04.032