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Synthesis of AKG 8. Reagents and conditions: (a) BF3.2MeOH, MeOH, 50 °C, 15 h, 75% of 13 and 4% of 14; (b) K2CO3, MeOH, rt, 42 h, quantitative conversion of 14 into 13; (c) MeI, NaOH, n-Bu4NBr, DMSO, rt, 18 h, 72%; (d) Red-Al, Et2O, 0 °C, 16 h, 82%; (e) MsCl, Et3N, DCM, −50 °C, 5 h, 74%; (f) KOH, n-Bu4NBr, DMSO, 35 °C, 14 h, 93%; (g) p-TsOH.H2O (0.05 equiv), MeOH/H2O (9:1), 60 °C, 5 h, 99%.
