ArticleJournal of the American Chemical Society2011
A stereocontrolled synthesis of (+)-saxitoxin.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Article
- Macrocycles of Saxitoxin: Insights into the Structure of Zetekitoxin AB.Chembiochem : a European journal of chemical biology · 2025Article
- Mass cultivation of the dinoflagellate Alexandrium pacificum for gonyautoxin-1,4 production.Scientific reports · 2025Article
- Synthesis of Saxitoxin Biosynthetic Intermediates: Reveal the Mechanism for Formation of its Tricyclic Skeleton in Biosynthesis.Chemistry, an Asian journal · 2024Article
- The Chemistry of Phytoplankton.Chemical reviews · 2024Review
- Chemical and Biological Tools for the Study of Voltage-Gated Sodium Channels in Electrogenesis and Nociception.Chembiochem : a European journal of chemical biology · 2022Review
- Divergent 2-Chloroquinazolin-4(3H)-one Rearrangement: Twisted-Cyclic Guanidine Formation or Ring-Fused N-Acylguanidines via a Domino Process.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Synthetic Approaches to Zetekitoxin AB, a Potent Voltage-Gated Sodium Channel Inhibitor.Marine drugs · 2019Review
- A Direct C11 Alkylation Strategy on the Saxitoxin Core: A Synthesis of (+)-11-Saxitoxinethanoic Acid.Organic letters · 2019Article
- Divergent Synthesis of Natural Derivatives of (+)-Saxitoxin Including 11-Saxitoxinethanoic Acid.Angewandte Chemie (International ed. in English) · 2019Article
- Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions.Organic letters · 2017Article
- Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.Organic letters · 2016Article
- A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products.Journal of visualized experiments : JoVE · 2016Article
- Biosynthetic route towards saxitoxin and shunt pathway.Scientific reports · 2016Article
- Preparation of a 1,2-isoxazolidine synthon for the synthesis of zetekitoxin AB.Tetrahedron letters · 2015Article
- Syntheses of Cyclic Guanidine-Containing Natural Products.Tetrahedron · 2015Article
- Synthetic studies towards Zetekitoxin AB: preparation of 4,5-epi-11-hydroxy-saxitoxinol.Tetrahedron · 2014Article
- Recent progress in neuroactive marine natural products.Natural product reports · 2014Review
- Synthesis of cyclic guanidines via Pd-catalyzed alkene carboamination.Organic letters · 2013Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
A concise stereoselective total synthesis of (+)-saxitoxin is described. A silver(I)-initiated hydroamination cascade constructs the bicyclic guanidinium ion core from a alkynyl bisguanidine. This sequence creates two C-N bonds, one C-O bond, and three rings and forms a single stereoisomer in a single synthetic transformation. This process enabled us to complete the synthesis of (+)-saxitoxin in 14 steps from N-Boc-l-serine methyl ester.
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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.