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Synthesis of betulin derivatives. Reagent and conditions: i. Jones oxidation, CrO3, aq. H2SO4, acetone, 0 °C, (N2 atm); ii. DMAP, pyridine, Ac2O, 0 °C; iii.NBS, CCl4; iv. MeOH/THF, 10% Pd/C, H2 (40 psi); v. DCM, PCC, 0 °C; vi. chloroform, 70%-mCPBA, 35 °C; vii. THF, LiAlH4, −40 °C; viii. imidazole, THF, TBDPSCl, −70 °C.
