By utilizing our recently developed enantioselective rhodium-catalyzed allylation<i>, we are attempting to synthesize the biologically active natural product (+)-chelidonine from sesamol (Scheme 1).Preliminary studies with a model substrate have indicated that the key rhodium catalyzed step proceeds with good yield, high enantioselectivity and provides a single diastereomer (Scheme 2).   <i> Y. Luo, H.B. Hepburn*, N. Chotsaeng, H.W. Lam, Angew. Chem. Int. Ed. 2012 , 51, 8309-8313, H.B. Hepburn*, N. Chotsaeng, Y. Luo, H.W. Lam, Synthesis, 2013 , 45, 2649-2661.

Studies towards the total synthesis of (+)-chelidonine using an enantioselective rhodium-catalyzed allylation of a cyclic imine

247th National Meeting (2014)

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