ArticleNature communications2015
Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars.
Article in Nature communications, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Stereoselective Chemoenzymatic Cascades for the Synthesis of Densely Functionalized Iminosugars.Journal of the American Chemical Society · 2025Article
- Flow Chemistry for Synthesis of 2-(C-Glycosyl)acetates from Pyranoses via Tandem Wittig and Michael Reactions.Organic process research & development · 2024Article
- Iminosugar-Based Nicotinamide Phosphoribosyltransferase (NAMPT) Inhibitors as Potential Anti-Pancreatic Cancer Agents.Pharmaceutics · 2023Article
- Diversity-oriented synthesis of glycomimetics.Communications chemistry · 2021Article
- Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications.RSC advances · 2020Review
- Thiol-ene "Click" Synthesis and Pharmacological Evaluation ofMolecules (Basel, Switzerland) · 2019Article
- A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K.Journal of the American Chemical Society · 2019Article
- Glycoside Mimics from Glycosylamines: Recent Progress.Molecules (Basel, Switzerland) · 2018Review
- The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold.Antiviral research · 2018Review
- Probing the Inhibitor versus Chaperone Properties of sp²-Iminosugars towards Human β-Glucocerebrosidase: A Picomolar Chaperone for Gaucher Disease.Molecules (Basel, Switzerland) · 2018Article
- Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases.Beilstein journal of organic chemistry · 2018Article
- Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides.Beilstein journal of organic chemistry · 2018Review
- Structural Snapshots for Mechanism-Based Inactivation of a Glycoside Hydrolase by Cyclopropyl Carbasugars.Angewandte Chemie (International ed. in English) · 2016Article
- Stereoselective Halogenation in Natural Product Synthesis.Angewandte Chemie (International ed. in English) · 2016Review
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Iminosugars have attracted increasing attention as chemical probes, chaperones and leads for drug discovery. Despite several clinical successes, their de novo synthesis remains a significant challenge that also limits their integration with modern high-throughput screening technologies. Herein, we describe a unique synthetic strategy that converts a wide range of acetaldehyde derivatives into iminosugars and imino-C-nucleoside analogues in two or three straightforward transformations. We also show that this strategy can be readily applied to the rapid production of indolizidine and pyrrolizidine iminosugars. The high levels of enantio- and diastereoselectivity, excellent overall yields, convenience and broad substrate scope make this an appealing process for diversity-oriented synthesis, and should enable drug discovery efforts.
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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.