ArticleNature chemistry2017
Reactions of hexadehydro-Diels-Alder benzynes with structurally complex multifunctional natural products.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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31 citing papers in PubMed, 115 citations in OpenAlex.
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- Chemical Reactions of Indole Alkaloids That Enable Rapid Access to New Scaffolds for Discovery.SynOpen (2017) · 2023Article
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- Cycloaddition Cascades of Strained Alkynes and Oxadiazinones.Angewandte Chemie (International ed. in English) · 2021Article
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- Mechanistic and Kinetic Factors of ortho-Benzyne Formation in Hexadehydro-Diels-Alder (HDDA) Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Total Synthesis of (-)-Strictosidine and Interception of Aryne Natural Product Derivatives "Strictosidyne" and "Strictosamidyne".Journal of the American Chemical Society · 2021Article
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- Highly Conjugated π-Systems Arising from Cannibalistic Hexadehydro-Diels-Alder Couplings: Cleavage of C-C Single and Triple Bonds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Ring-opening functionalizations of unstrained cyclic amines enabled by difluorocarbene transfer.Nature communications · 2020Article
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- Synthesis of Degraded Limonoid Analogs as New Antibacterial Scaffolds againstAntibiotics (Basel, Switzerland) · 2020Article
- Reactions of HDDA Benzynes withEuropean journal of organic chemistry · 2020Article
- The Aza-hexadehydro-Diels-Alder Reaction.Journal of the American Chemical Society · 2019Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
An important question in organic chemistry concerns the extent to which benzynes-one of the classical reactive intermediates in organic chemistry-can react in discriminating fashion with trapping reagents. In particular, whether these species can react selectively with substrates containing multiple functional groups and possible sites of reactivity has remained unanswered. Natural products comprise a palette of multifunctional compounds with which to address this question. Here, we show that benzynes produced by the hexadehydro-Diels-Alder (HDDA) reaction react with many secondary metabolites with a preference for one among several pathways. Examples demonstrating such selectivity include reactions with: phenolics, through dearomatizing ortho-substitution; alkaloids, through Hofmann-type elimination; tropolone and furan, through cycloaddition; and alkaloids, through three-component fragmentation-coupling reactions. We also demonstrate that the cinchona alkaloids quinidine and quinine give rise to products (some in as few as three steps) that enable subsequent and rapid access to structurally diverse polyheterocyclic compounds. The results show that benzynes are quite discriminating in their reactivity-a trait perhaps not broadly enough appreciated.
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