ArticleScience (New York, N.Y.)2014
Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence.
Article in Science (New York, N.Y.), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 39 papers.
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Who cites it
39 citing papers in PubMed.
- An Alkaloid Biosynthetic Gene Bundle in Animals.Journal of the American Chemical Society · 2026Article
- Divergent synthesis of Haplomitrium diterpenoids via a late-stage biomimetic skeletal reorganization approach.Nature communications · 2025Article
- Discovery, biosynthesis, and bioactivities of peptidic natural products from marine sponges and sponge-associated bacteria.Natural product reports · 2025Review
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- 10th anniversary of discovering cGAMP: synthesis and beyond.Organic chemistry frontiers : an international journal of organic chemistry · 2023Article
- Secondary metabolites from marine sponges of the genusRSC advances · 2022Review
- Asymmetric Total Syntheses, Stereostructures, and Cytotoxicities of Marine Bromotriterpenoids Aplysiol B (Laurenmariannol) and Saiyacenol A.Chemistry, an Asian journal · 2022Article
- Marine alkaloids as bioactive agents against protozoal neglected tropical diseases and malaria.Natural product reports · 2021Review
- Efficient construction of the hexacyclic ring core of palau'amine: the pChemical science · 2021Article
- Marine Pyrrole Alkaloids.Marine drugs · 2021Review
- Agelasine Diterpenoids and Cbl-b Inhibitory Ageliferins from the Coralline DemospongeMarine drugs · 2021Article
- Article
- An Updated Review on the Synthesis and Antibacterial Activity of Molecular Hybrids and Conjugates Bearing Imidazole Moiety.Molecules (Basel, Switzerland) · 2020Review
- Total Synthesis of (±)-Sceptrin.Organic letters · 2020Article
- Precursor-Guided Mining of Marine Sponge Metabolomes Lends Insight into Biosynthesis of Pyrrole-Imidazole Alkaloids.ACS chemical biology · 2020Article
- X-ray Crystallography and Unexpected Chiroptical Properties Reassign the Configuration of Haliclonadiamine.Journal of the American Chemical Society · 2020Article
- Article
- Bisindole Alkaloids from a New Zealand Deep-Sea Marine SpongeMarine drugs · 2019Article
- Aplysinopsin-type and Bromotyrosine-derived Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata.Scientific reports · 2019Article
- Bromopyrrole Alkaloids from the Sponge Agelas kosrae.Marine drugs · 2018Article
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11 authors.
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Abstract
Cycloaddition is an essential tool in chemical synthesis. Instead of using light or heat as a driving force, marine sponges promote cycloaddition with a more versatile but poorly understood mechanism in producing pyrrole-imidazole alkaloids sceptrin, massadine, and ageliferin. Through de novo synthesis of sceptrin and massadine, we show that sponges may use single-electron oxidation as a central mechanism to promote three different types of cycloaddition. Additionally, we provide surprising evidence that, in contrast to previous reports, sceptrin, massadine, and ageliferin have mismatched chirality. Therefore, massadine cannot be an oxidative rearrangement product of sceptrin or ageliferin, as is commonly believed. Taken together, our results demonstrate unconventional chemical approaches to achieving cycloaddition reactions in synthesis and uncover enantiodivergence as a new biosynthetic paradigm for natural products.
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