(8)S-HEPE synthesis

Yield:-

Steps:

Multi-step reaction with 6 steps
1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h / 20 °C / Cooling with ice
2.1: acetonitrile / 4 h / Reflux
3.1: sodium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 - 0 °C / Cooling with ice
3.2: 3 h / -78 - 0 °C
3.3: 23 h / 0 °C
4.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.42 h / -78 °C
4.2: 0.25 h / 0 °C
5.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -90 - 0 °C / Cooling with ice
5.2: 3 h / 0 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran; aq. phosphate buffer / 4 h / 20 °C / pH 5 / Cooling with ice

References:

Suganuma, Yuta;Saito, Shun;Kobayashi, Yuichi [Synlett,2019,vol. 30,# 3,p. 338 - 342]