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Synthesis of S-DPD by Maycock and Ventura. (a) TBDPSCl, Pyr, DMAP, rt, 97%; (b) LiOH, THF/H2O, rt, 94%; (c) HNMeOMe·Cl, DCC, CH2Cl2, rt, Δ, 85%; (d) BuLi, propyne, THF, −78 °C/0 °C, 95%; (e) (S)-Alpine borane, THF, rt, 67%; (f) TBAF, THF, rt, 86%; (g) 1,1-dimethoxycyclohexanone, H2SO4, DMF, 91%; (h) NaIO4, RuO2, CCl4/MeCN, rt, 86%; (i) Dowex 50WX8, H2O, pH 3, rt.
