3.1.8. (3*S*,4*S*)-4-methoxy-5,8-bis(methoxymethoxy)-3-pentyl-7-phenylisochroman-1-one (**9a**)

Bromo compound **3** (10.0 mg, 22.4 μmol), Cs2CO3 (21.9 mg, 67.1 μmol), phenylboronic acid (5.5 mg, 44.7 μM), and PdCl2(PPh3)2 (3.1 mg, 44.7 μmol) were dissolved in degassed dioxane (0.22 mL) at room temperature. After stirring for 1 h under reflux condition, the reaction was quenched by adding saturated aqueous NH4Cl. The mixture was extracted with EtOAc (×3) and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified with flash column chromatography (EtOAc:*n*-hexane = 3:7) to give diMOM-protected phenyl derivative **9a** (7.4 mg, 75%) as a white wax. 1H-NMR (500 MHz, CDCl3) δ 7.55 (1H, d, *J* = 7.6 Hz), 7.50-7.38 (3H, overlapped), 7.36 (1H, dd, *J* = 7.3 Hz), 5.25 (2H, s), 4.80 (2H, s), 4.66 (1H, s), 4.33 (1H, t, *J* = 7.0 Hz), 3.50 (3H, s), 3.37 (3H, s), 2.92 (3H, s), 2.06 (1H, m), 1.85 (1H, m), 1.70–1.50 (1H, overlapped), 1.50–1.25 (5H, overlapped), 0.92 (3H, br-s); 13C-NMR (125 MHz, CDCl3) δ 162.1, 150.5, 150.0, 139.5, 137.9, 129.8, 128.3, 128.1, 127.7, 121.0, 119.9, 101.0, 95.1, 80.8, 68.3, 57.1, 56.4, 31.6, 30.6, 24.9, 22.5, 14.0.; IR (KBr) 2956, 2927, 2859, 2828, 1728, 1467, 1152, 1008, 932 cm<sup>−</sup>1; HRMS (ESI) *m*/*z* (M + Na)<sup>+</sup> calculated for (C25H32O7Na)<sup>+</sup> 467.2046, found 467.2043.
