ArticleJournal of the American Chemical Society2014
Synthesis and biological evaluation of QRSTUVWXYZA' domains of maitotoxin.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 42 citations in OpenAlex.
- Efficient Synthesis of Fused Polycyclic Ether Systems via Sulfonium Ylides: A Synthetic Approach to Yessotoxin and Adriatoxin.Marine drugs · 2025Article
- The Chemistry of Phytoplankton.Chemical reviews · 2024Review
- Directional Ionic Bonds.Journal of the American Chemical Society · 2023Article
- Synthesis of C-Oligosaccharides through Versatile C(spAngewandte Chemie (International ed. in English) · 2022Article
- Marine Heterocyclic Compounds That Modulate Intracellular Calcium Signals: Chemistry and Synthesis Approaches.Marine drugs · 2021Review
- Perspectives from nearly five decades of total synthesis of natural products and their analogues for biology and medicine.Natural product reports · 2020Review
- Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes.Organic letters · 2019Article
- Ladder-Shaped Ion Channel Ligands: Current State of Knowledge.Marine drugs · 2017Review
- Biomimetic molecular design tools that learn, evolve, and adapt.Beilstein journal of organic chemistry · 2017Review
Corrections and comments
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Authors and funding
6 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The synthesis of QRSTUVWXYZA' domains 7, 8, and 9 of the highly potent marine neurotoxin maitotoxin (1), the largest secondary metabolite isolated to date, is described. The devised synthetic strategy entailed a cascade Takai-Utimoto ester olefination/ring closing metathesis to construct ring Y, a hydroxydithioketal cyclization/methylation sequence to cast ring X, a Horner-Wadsworth-Emmons coupling of WXYZA' ketophosphonate 11 with QRSTU aldehyde 12 to form enone 10, and a reductive hydroxyketone ring closure to forge ring V. 2D NMR spectroscopic analysis and comparison of (13)C chemical shifts with those of the corresponding carbons of maitotoxin revealed close similarities supporting the originally assigned structure of this region of the natural product. Biological evaluations of various synthesized domains of maitotoxin in this and previous studies from these laboratories led to fragment structure-activity relationships regarding their ability to inhibit maitotoxin-elicited Ca(2+) influx in rat C6 glioma cells.
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