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Synthesis of C20-O-trityl-prostratin-ol (10). Reagents and conditions: (a) H2SO4, H2O, 90 °C, 40% yield; (b) trityl chloride, pyridine, 50 °C, 94–96% yield; (c) N2H4•H2O, AcOH, MeOH; (d) iPr2NEt, toluene, 140 °C, then Pb(OAc)4, CH2Cl2, −78 °C → room temperature, 50–59% yield over two steps; (e) hν (350 nM), EtOAc, 64% yield; and (f) Ba(OH)2•8H2O, MeOH, 89% yield.
