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Synthesis of AKG 10. Reagents and conditions: (a) MsCl, Et3N, DCM, −10 °C, 4 h, 65%; (b) NaN3, DMSO, 80 °C, 18 h, 80%; (c) Dibal, Et2O, −80 °C, 2 h, 68%; (d) NaBH4, EtOH, 0 °C, 1 h, 74%; (e) MsCl, Et3N, DCM, −50 °C, 4 h and then up to −5 °C, 59%; (f) 18, 50% aqueous NaOH, n-Bu4NBr, DMSO, 40 °C, 15 h; (g) maleic anhydride, cyclohexane, 72 h, 45 °C; (h) p-TsOH.H2O (0.05 equiv), MeOH/H2O (9:1), 60 °C, 5 h, 97%.
