ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
Irreversible endo-selective diels-alder reactions of substituted alkoxyfurans: a general synthesis of endo-cantharimides.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- A Computational/Experimental Investigation into the Reversibility of [6+4]/[4+2] Cycloadditions with Tropone Derivatives.The Journal of organic chemistry · 2026Article
- The Interplay between Kinetics and Thermodynamics in Furan Diels-Alder Chemistry for Sustainable Chemicals Production.Angewandte Chemie (International ed. in English) · 2022Review
- Furoic acid and derivatives as atypical dienes in Diels-Alder reactions.Green chemistry : an international journal and green chemistry resource : GC · 2021Article
- Mechanically Triggered Release of Functionally Diverse Molecular Payloads from Masked 2-Furylcarbinol Derivatives.ACS central science · 2021Article
- Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules.European journal of organic chemistry · 2018Article
- Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene.Organic & biomolecular chemistry · 2017Article
- Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology.Angewandte Chemie (International ed. in English) · 2016Article
Corrections and comments
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Authors and funding
7 authors.
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Abstract
The [4+2] cycloaddition of 3-alkoxyfurans with N-substituted maleimides provides the first general route for preparing endo-cantharimides. Unlike the corresponding reaction with 3H furans, the reaction can tolerate a broad range of 2-substitued furans including alkyl, aromatic, and heteroaromatic groups. The cycloaddition products were converted into a range of cantharimide products with promising lead-like properties for medicinal chemistry programs. Furthermore, the electron-rich furans are shown to react with a variety of alternative dienophiles to generate 7-oxabicyclo[2.2.1]heptane derivatives under mild conditions. DFT calculations have been performed to rationalize the activation effect of the 3-alkoxy group on a furan Diels-Alder reaction.
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