(E)-Methyl 3-phenyloct-2-enoate could be produced through the following synthetic routes.

(E)-Methyl 3-phenyloct-2-enoate (1). A 200-mL two-necked round-bottomed flask equipped with a magnetic stirring bar (2.5 cm × 0.8 cm) is charged with methyl 2-octynoate (5.00 mL, 4.60 g, 29.5 mmol), MeOH (60 mL) and phenylboronic acid (5.52 g, 44.3 mmol, 1.5 equiv). One neck of the flask is equipped with rubber septum and nitrogen inlet, the other with a glass stopper, and the reaction mixture is degassed once at -78 °C. The glass stopper is removed and CuOAc (84.0 mg, 0.606 mmol) is added. The reaction mixture is degassed three times at -78 °C. After vigorous stirring for 24 h at 28 °C under an N₂ atmosphere, the reaction mixture is filtered through a pad of Celite® and washed with a mixture of hexanes/EtOAc (150:1; 3x10 mL) to remove insoluble materials. The filtrate is concentrated by rotary evaporation (5.5 mmHg) at 30 °C to afford a crude oil. The crude product is purified by chromatography on SiO₂ to yield 1 (6.48 g, 94%) as a colorless oil.