Enantioselective de Novo Synthesis of 4-Deoxy-d-hexopyranoses via Hetero-Diels–Alder Cycloadditions: Total Synthesis of Ezoaminuroic Acid and Neosidomycin

2011 ◽  
Vol 76 (23) ◽  
pp. 9687-9698 ◽  
Author(s):  
Denis Giguère ◽  
Julien Martel ◽  
Tze Chieh Shiao ◽  
René Roy
Keyword(s):  
Total Synthesis ◽  
De Novo ◽  
Diels Alder ◽  
De Novo Synthesis

scholarly journals De novo synthesis, structural assignment and biological evaluation of pseudopaline, a metallophore produced by Pseudomonas aeruginosa

2019 ◽  
Vol 10 (27) ◽  
pp. 6635-6641 ◽  
Author(s):  
Jian Zhang ◽  
Tianhu Zhao ◽  
Rongwen Yang ◽  
Ittipon Siridechakorn ◽  
Sanshan Wang ◽  
...  
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Total Synthesis ◽  
Natural Product ◽  
Absolute Configuration ◽  
De Novo ◽  
Biological Evaluation ◽  
De Novo Synthesis ◽  
Structural Assignment ◽  
The Absolute

The first total synthesis and isolation of pseudopaline was reported, which allows determination and confirmation of the absolute configuration of the natural product.

scholarly journals Strategies for the De Novo Synthesis of Highly Substituted Pyridine Scaffolds: Unified Total Synthesis of the Limonoid Alkaloids

2021 ◽  
Author(s):  
Timothy Newhouse ◽  
Alexander Schuppe ◽  
Yannan Liu ◽  
Yizhou Zhao ◽  
Sebastian Ibarran ◽  
...  
Keyword(s):  
Total Synthesis ◽  
De Novo ◽  
Biologically Active ◽  
Synthetic Analog ◽  
De Novo Synthesis ◽  
Xylocarpus Granatum ◽  
Benzylic Oxidation ◽  
Substituted Pyridines ◽  
Active Natural ◽  
Core Framework

Highly substituted pyridine scaffolds are found in many biologically active natural products and therapeutics. Accordingly, numerous complementary de novo approaches to obtain differentially substituted pyridines have been disclosed. This article delineates the evolution of the synthetic strategies designed to assemble the demanding tetrasubstituted pyridine core present in the limonoid alkaloids isolated from Xylocarpus granatum, including xylogranatopyridine B, granatumine A and related congeners. The most efficient and convergent construction of the core framework present in xylogranatopyridine B involved a Liebeskind pyridine synthesis and late-stage benzylic oxidation. By contrast, the synthesis of the bislactone limonoid alkaloids, such as granatumine A which exhibited moderate PTP1B-inhibitory activities, necessitated the development of a novel pyran-to-pyridine conversion. In addition, NMR calculations suggested structural misassignment of several limonoid alkaloids, and predicted their C3-epimers as the correct structures, which was further validated unequivocally through chemical synthesis. While preliminary results of the pNPP assays showed that these bislactone limonoid alkaloids were only weakly inhibitory against PTP1B, C3-deoxy-xylogranatin F, an unnatural synthetic analog, was demonstrated to be more potent than the other congeners.

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