ArticleNature chemistry2014
Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction.
Article in Nature chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. It is linked to trial NCT07215273 (A Phase 2, Multicenter, Randomized, Double-blind Study of Safety and Efficacy of EL219), which is not on this map. Cited by 57 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
A Phase 2, Multicenter, Randomized, Double-blind Study of Safety and Efficacy of EL219 (Turletricin) Versus Liposomal Amphotericin B or Voriconazole for Early Antifungal Therapy of Invasive Mould Infections (TREAT-1)
Who cites it
57 citing papers in PubMed.
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- Derivatization of 2,1,3-Benzothiadiazole via Regioselective C-H Functionalization and Aryne Reactivity.The Journal of organic chemistry · 2024Article
- Chemical structure metagenomics of microbial natural products: surveying nonribosomal peptides and beyond.Beilstein journal of organic chemistry · 2024Article
- Catalytic Dienylation: An Emergent Strategy for the Stereoselective Construction of Conjugated Dienes and Polyenes.Synthesis · 2023Article
- Stepwise on-demand functionalization of multihydrosilanes enabled by a hydrogen-atom-transfer photocatalyst based on eosin Y.Nature chemistry · 2023Article
- Structural identification of pyridinopyrone compounds with anti-neuroinflammatory activity from streptomyces sulphureus DSM 40104.Frontiers in microbiology · 2023Article
- Photo-Induced Homologation of Carbonyl Compounds for Iterative Syntheses.Angewandte Chemie (International ed. in English) · 2022Article
- Haloboration: scope, mechanism and utility.New journal of chemistry = Nouveau journal de chimie · 2021Review
- Automated synthesis of prexasertib and derivatives enabled by continuous-flow solid-phase synthesis.Nature chemistry · 2021Article
- Z-Selective Dienylation Enables Stereodivergent Construction of Dienes and Unravels a Ligand-Driven Mechanistic Dichotomy.ACS catalysis · 2021Article
- Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes.Molecules (Basel, Switzerland) · 2021Review
- Deep Learning for Prediction and Optimization of Fast-Flow Peptide Synthesis.ACS central science · 2020Article
- Dienedioic acid as a useful diene building block via directed Heck-decarboxylate coupling.Communications chemistry · 2020Article
- Synthesis of Cross-Conjugated Polyenes via Palladium-Catalyzed Oxidative C-C Bond Forming Cascade Reactions of Allenes.The Journal of organic chemistry · 2020Article
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- Synthesis of (E,E)-Dienones and (E,E)-Dienals via Palladium-Catalyzed γ,δ-Dehydrogenation of Enones and Enals.iScience · 2019Article
Corrections and comments
- Commented on by
- Erratum issued
Authors and funding
3 authors.
Funding
Abstract
The inherent modularity of polypeptides, oligonucleotides and oligosaccharides has been harnessed to achieve generalized synthesis platforms. Importantly, like these other targets, most small-molecule natural products are biosynthesized via iterative coupling of bifunctional building blocks. This suggests that many small molecules also possess inherent modularity commensurate with systematic building block-based construction. Supporting this hypothesis, here we report that the polyene motifs found in >75% of all known polyene natural products can be synthesized using just 12 building blocks and one coupling reaction. Using the same general retrosynthetic algorithm and reaction conditions, this platform enabled both the synthesis of a wide range of polyene frameworks that covered all of this natural-product chemical space and the first total syntheses of the polyene natural products asnipyrone B, physarigin A and neurosporaxanthin b-D-glucopyranoside. Collectively, these results suggest the potential for a more generalized approach to making small molecules in the laboratory.
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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.