Multi-step reaction with 9 steps
1.1: diisobutylaluminium hydride / diethyl ether; hexane / -78 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
2.2: 0.5 h / -78 - 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C
3.2: 1 h / 0 - 20 °C / Reflux
4.1: diisobutylaluminium hydride / diethyl ether; hexane / -78 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
5.2: 0.5 h / -78 - 20 °C
6.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C / Inert atmosphere
6.2: 1 h / Inert atmosphere
7.1: diisobutylaluminium hydride / diethyl ether; hexane / -78 °C
8.1: Dimethyl ether; triethylamine / dichloromethane / 0.25 h / 0 °C
8.2: 1.5 h / 25 °C
9.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
9.2: 0.75 h / Inert atmosphere
With
N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; 18-crown-6 ether; Dimethyl ether; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; mineral oil;
2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Horner-Wadsworth-Emmons olefination / 3.2: Horner-Wadsworth-Emmons olefination / 5.1: Swern oxidation / 5.2: Swern oxidation;
DOI:10.1021/jo202602n