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Semi-synthesis of garcinoic acid from δ-tocotrienol. Reagents and conditions: (a) Ac2O, Et3N, CH2Cl2, 0 °C, 10 h, 90%; (b) PhSeCl, NCS, CH2Cl2, rt, 2 h; (c) 2,4,6-collidine, AgBF4, acetone, water, 60–70 °C, 4 h, 26% for 19 and 32% for 20; (d) (i) MsCl, pyridine, DMAP, 0 °C–rt, 1 h; (ii) acetone/H2O, NaOAc, reflux, 3 h, 34%; (e) DMP, CH2Cl2, 0 °C–rt, 1 h, 92%; (f) NaClO2, NaH2PO4, 2-methyl-2-butene, t-BuOH/H2O, 0 °C–rt, 80%; (g) (i) K2CO3, MeOH; (ii) 1N HCl, 85%.
