ArticleChemical science2023
Divergent total syntheses of ITHQ-type bis-β-carboline alkaloids by regio-selective formal aza-[4 + 2] cycloaddition and late-stage C-H functionalization.
Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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1 citing paper in PubMed, 6 citations in OpenAlex.
- Picrasidine S Induces cGAS-Mediated Cellular Immune Response as a Novel Vaccine Adjuvant.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
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4 authors at 1 institution in 1 country.
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Abstract
We herein report the first total syntheses of several bis-β-carboline alkaloids, picrasidines G, S, R, and T, and natural product-like derivatives in a divergent manner. Picrasidines G, S, and T feature an indolotetrahydroquinolizinium (ITHQ) skeleton, while picrasidine R possesses a 1,4-diketone linker between two β-carboline fragments. The synthesis of ITHQ-type bis-β-carboline alkaloids could be directly achieved by a late-stage regio-selective aza-[4 + 2] cycloaddition of vinyl β-carboline alkaloids, suggesting that this remarkable aza-[4 + 2] cycloaddition might be involved in the biosynthetic pathway. Computational studies revealed that such aza-[4 + 2] cycloaddition is a stepwise process and explained the unique regioselectivity (ΔΔ
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