“…After acidification with 2 N HCl to pH 2.0, the solution was extracted with EtOAc (3 × 50 mL). The organic layers were combined, dried with MgSO 4 , and concentrated in vacuo . Column chromatography (SiO 2 , pentane/EtOAc, 10:1) gave the product 15 (0.99 g, 4.36 mmol, 66%) as a yellowish oil: R f (SiO 2 , pentane/EtOAc, 10:1) 0.20; GC (ZB-5 MSi, MSTFA derivative) I 1857; IR (ATR) ν max 3005 (m), 2924 (s), 2855 (s), 2671 (w), 1707 (s), 1460 (m), 1413 (m), 1278 (m), 1227 (m), 935 (m), 725 (m) cm –1 ; 1 H NMR (CDCl 3 , 400 MHz) δ 7.19 (s, 1H, OH), 5.22–5.33 (m, 2H, HCCH), 2.28 (t, 2H, J = 7.7 Hz, CH 2 COOH), 1.92–1.99 (m, 4H, H 2 CHCCHC H 2 ), 1.54–1.61 (m, 2H, CH 2 CH 3 ), 1.13–1.37 (m, 12H, 6 × CH 2 ), 0.81 (t, 3H, J = 7.2 Hz, CH 3 ); 13 C NMR (CDCl 3 , 100 MHz) δ 180.3 (CO), 129.8 (HCCH), 34.1 ( C H 2 COOH), 31.8 (CH 2 ), 29.5 (2 × CH 2 ), 28.9 (2 × CH 2 ), 27.1 (H 2 C HCCH C H 2 ), 24.6 (CH 2 ), 22.6 ( C H 2 CH 3 ), 14.1 (CH 3 ); EIMS m / z (MSTFA derivative) 298 [M] + (21), 283 [M + -CH 3 ] (96), 255 (5), 227 (5), 199 (29), 183 (11), 166 (48), 145 (54), 117 (100), 96 (44), 73 (93), 55 (58), 39 (10).…”