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Synthesis of (S)-(+)-pelletierine and (S)-(−)-coniine. Formal synthesis of (−)-lasubine II and (+)-cermizine C.12
i) Pd(OH)2 (1.0 eq), H2 (1 atm), MeOH, rt, 48 h; ii) CF3CO2H, CH2Cl2, 0 °C, 2 h, then NaOH, pH 10; iii) PdCl2 (1.0 eq), CuCl (10 mol%), O2, DMF/H2O (10:1), rt, 10 h; iv) CF3CO2H, CH2Cl2, 0 °C, 2 h, then NaOH.
