ArticleChemical science2010
Total synthesis of all (-)-Agelastatin alkaloids.
Article in Chemical science, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 90 citations in OpenAlex.
- A general approach to stereospecific Pd-catalyzed cross-coupling reactions of benzylic stereocenters.Chemical science · 2023Article
- TheMolecules (Basel, Switzerland) · 2023Article
- Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A.Organic letters · 2023Article
- Marine Pyrrole Alkaloids.Marine drugs · 2021Review
- Synthesis of Agelastatin A and Derivatives Premised on a Hidden Symmetry Element Leading to Analogs Displaying Anticancer Activity.Tetrahedron · 2021Article
- Recent progress toward the asymmetric synthesis of carbon-substituted piperazine pharmacophores and oxidative related heterocycles.RSC medicinal chemistry · 2020Review
- Synthesis and Evaluation of Agelastatin Derivatives as Potent Modulators for Cancer Invasion and Metastasis.The Journal of organic chemistry · 2017Article
- Inhibition of Eukaryotic Translation by the Antitumor Natural Product Agelastatin A.Cell chemical biology · 2017Article
- Derivatization of agelastatin A leading to bioactive analogs and a trifunctional probe.Bioorganic & medicinal chemistry letters · 2016Article
- The fibroblast Tiam1-osteopontin pathway modulates breast cancer invasion and metastasis.Breast cancer research : BCR · 2016Article
- Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.Journal of the American Chemical Society · 2016Article
- Synthesis of 2-Aminoazoles from Thioesters via α-Heterosubstituted Ketones by Copper-Mediated Cross-Coupling.The Journal of organic chemistry · 2015Article
- 10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D.Angewandte Chemie (International ed. in English) · 2015Article
- Biogenetically-inspired total synthesis of epidithiodiketopiperazines and related alkaloids.Accounts of chemical research · 2015Article
- Syntheses of Cyclic Guanidine-Containing Natural Products.Tetrahedron · 2015Article
- Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.Chemical communications (Cambridge, England) · 2014Review
- Potent fluorinated agelastatin analogues for chronic lymphocytic leukemia: design, synthesis, and pharmacokinetic studies.Journal of medicinal chemistry · 2014Article
- NHC-Cu-catalyzed addition of propargylboron reagents to phosphinoylimines. Enantioselective synthesis of trimethylsilyl-substituted homoallenylamides and application to the synthesis of S-(-)-cyclooroidin.Journal of the American Chemical Society · 2014Article
- Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.The Journal of organic chemistry · 2014Article
- Synthesis and anticancer activity of all known (-)-agelastatin alkaloids.The Journal of organic chemistry · 2013Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The pyrrole-imidazole family of marine alkaloids, derived from linear clathrodin-like precursors, constitutes a diverse array of structurally complex natural products. The bioactive agelastatins are members of this family that possess a tetracyclic molecular framework incorporating C4-C8 and C7-N12 bond connectivities. We provide a hypothesis for the formation of the unique agelastatin architecture that maximally exploits the intrinsic chemistry of plausible biosynthetic precursors. We report the concise enantioselective total syntheses of all known agelastatin alkaloids including the first total syntheses of agelastatins C, D, E, and F. Our gram-scale chemical synthesis of agelastatin A was inspired by our hypothesis for the biogenesis of the cyclopentane C-ring and required the development of new transformations including an imidazolone-forming annulation reaction and a carbohydroxylative trapping of imidazolones.
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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.