ArticleChemical science2021
Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Recent advances in microbially derived chlorinated antiparasitic compounds.Molecular diversity · 2025Review
- Synthesis of the 5/5-spiroindimicin alkaloids: development of a general synthetic approach and biological investigations.Organic & biomolecular chemistry · 2024Article
- Advances in the total synthesis of bis- and tris-indole alkaloids containing N-heterocyclic linker moieties.Natural product reports · 2024Review
- Easy one-pot synthesis of multifunctionalized indole-pyrrole hybrids as a new class of antileishmanial agents.RSC advances · 2024Article
- Recent advances in oxidative phenol coupling for the total synthesis of natural products.Natural product reports · 2024Review
- Review
- Prediction of Antileishmanial Compounds: General Model, Preparation, and Evaluation of 2-Acylpyrrole Derivatives.Journal of chemical information and modeling · 2022Article
- Symmetry-Driven Total Synthesis of Myrioneurinol.Journal of the American Chemical Society · 2022Article
- Recent Progress in the Development of Indole-Based Compounds Active against Malaria, Trypanosomiasis and Leishmaniasis.Molecules (Basel, Switzerland) · 2022Review
- Marine Pyrrole Alkaloids.Marine drugs · 2021Review
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Authors and funding
10 authors.
Funding
Abstract
The spiroindimicins are a unique class of chlorinated indole alkaloids characterized by three heteroaromatic rings structured around a congested spirocyclic stereocenter. Here, we report the first total synthesis of (+)-spiroindimicin A, which bears a challenging C-3'/C-5''-linked spiroindolenine. We detail our initial efforts to effect a biomimetic oxidative spirocyclization from its proposed natural precursor, lynamicin D, and describe how these studies shaped our final abiotic 9-step solution to this complex alkaloid built around a key Pd-catalyzed asymmetric spirocyclization. Scalable access to spiroindimicins A, H, and their congeners has enabled discovery of their activity against several parasites relevant to human health, providing potential starting points for new therapeutics for the neglected tropical diseases leishmaniasis and African sleeping sickness.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.