Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates
The first asymmetric total synthesis of the bisbenzylisoquinoline alkaloids berbamine (<b>1a</b>) and oxyacanthine (<b>1b</b>) has been accomplished by employing Noyori asymmetric hydrogenation for chirality installation and leveraging copper-mediated Ullmann coupling for mac...
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2025
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| Summary: | The first asymmetric total synthesis of the bisbenzylisoquinoline alkaloids berbamine (<b>1a</b>) and oxyacanthine (<b>1b</b>) has been accomplished by employing Noyori asymmetric hydrogenation for chirality installation and leveraging copper-mediated Ullmann coupling for macrocycle formation. Our synthesis unequivocally confirmed the sample misidentification of <b>1a</b>, as indicated in our previous work. Evaluation of anti-inflammatory activities revealed that both synthetic and natural berbamine or oxyacanthine comparably suppressed gene expression of pro-inflammatory cytokines IL-6 and IL-1β in LPS-stimulated RAW 264.7 macrophages. Notably, intermediate <b>15a</b> displayed potent anti-inflammatory activity coupled with minimal cytotoxicity, emerging as a promising lead candidate for the development of novel anti-inflammatory agents. |
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