Fig. 4 in A comprehensive review: Biological activity, modification and synthetic methodologies of prenylated flavonoids

Fig. 4. Synthesis of antiproliferative prenyl flavonoid derivatives (197–207). Reagents and conditions: (a) CH CN, ZnCl, Et O, HCl g, 0–5 ◦ C; (b) H O, reflux, 2 h; 3 2 2 2 (c) Me SO, K CO, acetone, rt, 0.5 h; (d) benzaldehyde or p-anisaldehyde, KOH, EtOH, H O, rt, 3 h; (e) CH –CHCH Br, K CO, acetone, reflux, 12 h; (f) heat, 2 4 2 3 2 2– 2 2 3 210 ◦ C, 4 h; (g) CH COONa, C H OH, reflux, 24 h; (h) I, pyridine, 90 ◦ C, 16 h; (i) KMnO, HIO, i-PrOH, H O, rt; (j) R R CHP + Ph3Br, n-BuLi, THF, rt, 24 h; (k) 1 3 2 5 2 4 4 2 2 3 equiv BBr3, ClCH2CH2Cl, rt, 2 h; (l) 8 equiv BBr3, ClCH2CH2Cl, reflux, 4 h.