ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Development of an Allenyne-Alkyne [4+2] Cycloaddition and its Application to Total Synthesis of Selaginpulvilin A.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed.
- Utilizing the Pentadehydro-Diels-Alder Reaction for Polycyclic Aromatic Compound Synthesis: Diels-Alder-Based Linker Transformation.Molecules (Basel, Switzerland) · 2025Article
- An Untethered and Formal Intermolecular Hexadehydro-Diels-Alder Reaction: Alkynylboronates with 2-(1,3-Butadiynyl)pyridines.Journal of the American Chemical Society · 2024Article
- Free carbenes from complementarily paired alkynes.Nature chemistry · 2024Article
- Development of an Allenyne-Alkyne [4+2] Cycloaddition and its Application to Total Synthesis of Selaginpulvilin A.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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5 authors.
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Abstract
A new [4+2] cycloaddition of allenyne-alkyne is developed. The reaction is believed to proceed with forming an α,3-dehydrotoluene intermediate. This species behaves as a σπ-diradical to react with a hydrogen atom donor, whereas it displays a zwitterionic reactivity toward weak nucleophiles. The efficiency of trapping α,3-dehydrotoluene depends not only on its substituents but also the trapping agents. Notable features of the reaction are the activating role of the extra alkyne of the 1,3-diyne that reacts with the allenyne moiety and the opposite mode of trapping with oxygen and nitrogen nucleophiles. Oxygen nucleophiles result in the oxygen-end incorporation at the benzylic position of the α,3-dehydrotoluene, whereas with amine nucleophiles the nitrogen-end is incorporated into the aromatic core. Relying on the allenyne-alkyne cycloaddition as an enabling strategy, a concise total synthesis of phosphodiesterase-4 inhibitory selaginpulvilin A is realized.
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