Efficient construction of the hexacyclic ring core of palau'amine: the pKa concept for proceeding with unfavorable equilibrium reactions
Author:
Affiliation:
1. Graduate School of Pharmaceutical Sciences, Tokushima University, 1-78 Shomachi, Tokushima, 770-8505, Japan
2. Research Cluster on “Innovative Chemical Sensing”, Tokushima University, 1-78 Shomachi, Tokushima, 770-8505, Japan
Abstract
Funder
Japan Society for the Promotion of Science
Nagase Science Technology Foundation
Suntory Foundation
University of Tokushima
Publisher
Royal Society of Chemistry (RSC)
Subject
General Chemistry
Link
http://pubs.rsc.org/en/content/articlepdf/2021/SC/D1SC03260G
Reference65 articles.
1. A Submarine Journey: The Pyrrole-Imidazole Alkaloids
2. Sponge's Molecular Diversity Through the Ambivalent Reactivity of 2-Aminoimidazole: A Universal Chemical Pathway to the Oroidin-Based Pyrrole-Imidazole Alkaloids and Their Palau'amine Congeners
3. Palau'amine: a cytotoxic and immunosuppressive hexacyclic bisguanidine antibiotic from the sponge Stylotella agminata
4. Palau'amine and Its Congeners: A Family of Bioactive Bisguanidines from the Marine Sponge Stylotella aurantium1
5. Structural Assignment of Tetrabromostyloguanidine: Does the Relative Configuration of the Palau'amines Need Revision?
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1. Utilizing the pKa Concept to Address Unfavorable Equilibrium Reactions in the Total Synthesis of Palau’amine;Modern Natural Product Synthesis;2024
2. One-Pot Synthesis of Unprotected 2-Acylpyrroles from 1,2,3-Triazoles and 2-Hydroxymethylallyl Carbonates;The Journal of Organic Chemistry;2022-12-20
3. Silver-Catalyzed Synthesis of CF3-Substituted 2-Imidazolines;Chinese Journal of Organic Chemistry;2022
4. Synthesis of bridgehead-azacycles via dual C–N/C–C annulation of α-amino acids, aminals and maleimides;Organic & Biomolecular Chemistry;2022
5. Fine-Tuning of Acid–Base Equilibria on the Synthesis of the Hexacyclic Core of Palau’amine;Synfacts;2021-10-19
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