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Total synthesis reports high enantioselectivity in tacaman alkaloids, implying efficient construction methods for complex scaffolds.
The subgram-scale total synthesis of the tacaman alkaloids (−)-tacamine, (+)-tacamonine, (+)-17-β-hydroxytacamonine, and (−)-decarbomethoxytacamine is reported. Our approach prominently features a unified, highly enantioselective Ir-catalyzed hydrogenation of Wenkert's enamide analogues. This method enables the construction of a series of cis-fused indoloquinolizidine scaffolds with exceptional reaction efficiency and enantioselectivities, achieving yields of up to 98% and enantiomeric excesses (ee) of up to 99%.
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Lin et al. (2025) studied this question.
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